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Prediction of hepatotoxicity in humans remains an unresolved challenge. Recently, an in-vitro/in-silico-method was established to predict blood concentrations of test compounds with an increased risk of causing human hepatotoxicity. In the present study, we addressed the question whether gene expression data can improve the quality of hepatotoxicity prediction compared to cytotoxicity analysis alone. A particular challenge is that high-dimensional gene expression data must be summarized into variables that allow for the determination of the lowest test compound concentration that causes altered gene expression. To address this challenge, we analyzed 60 hepatotoxic and non-hepatotoxic substances in a concentration dependent manner for cytotoxicity and expression of 3,524 probes, whose expression were previously reported to be influenced by hepatotoxicants. The toxicity separation index (TSI) was applied to quantify how well specific summary variables of gene expression are able to differentiate between the set of hepatotoxic and non-hepatotoxic substances. The best TSI was obtained when the lowest concentration of a test compound was considered positive that led to differential expression of two genes when compared to vehicle controls. Furthermore, the best gene expression-based summary variable was superior to cytotoxicity-based variables alone, and the combination of the best summary variables of gene expression and cytotoxicity data further improved the TSI compared to each category alone. In conclusion, the method used to derive summary variables of gene expression is critical and the best summary variables improve the prediction of hepatotoxic substances in relation to oral doses and blood concentrations in humans.

A series of windmill-shape heterocyclic molecules containing three N-B←N units, TBN and its derivatives, with quasi-planar C 3 symmetric backbone, are synthesized. The parent TBN exhibits a strongly allowed, doubly degenerate lowest excited state but suffers from very low fluorescence, due to very fast nonradiative decay rate through a conical intersection (CI) as revealed by femtosecond transient absorption spectroscopy and quantum-chemical calculations. Introducing peripheral phenyl- or thienyl-groups (Ph-TBN or Th-TBN) induces pronounced bathochromic shifts and enhances fluorescence, which is beneficial from inhibited nonradiative pathway by the increased energy barriers to access the CI at excited state. The understanding of this rather uncommon behaviour may open routes for the design of novel fluorescence materials., (© 2024 Wiley-VCH GmbH.)

We showcase herein organic crystalline solid solutions (CSSs) based on the simplest polycyclic aromatic hydrocarbon (PAH) scaffold, naphthalene, stabilized by dispersion forces induced by adamantane substitution. High thermal stability of the host and guest molecules synthesized by cross-coupling of dibromonaphthalene derivatives and 4-(1-adamantyl)phenyl boronic ester enabled formation of crystals by sublimation. We could generate binary monocrystalline solid solution systems proven by X-ray crystallography, the first system of designed CSSs stabilized exclusively via dispersion forces with structural evidence. These observations are additionally supported by lattice energy calculations and spectroscopic examinations. For the generation of CSSs, it is of utmost importance that the host and guest molecules have similar lattice energies and spatial compatibility. We anticipate that the thermostable organic CSS design demonstrated herein would be beneficial for functional materials and further investigation towards materials with unique properties., (© 2024 The Authors. ChemPlusChem published by Wiley-VCH GmbH.)

We investigated the role of alpha in the suppression of attention capture by salient but to-be-suppressed (negative and nonpredictive) color cues, expecting a potential boosting effect of alpha-rhythmic entrainment on feature-specific cue suppression. We did so by presenting a rhythmically flickering visual bar of 10 Hz before the cue - either on the cue's side or opposite the cue -while an arrhythmically flickering visual bar was presented on the respective other side. We hypothesized that rhythmic entrainment at cue location could enhance the suppression of the cue. Testing 27 participants ranging from 18 to 39 years of age, we found both behavioral and electrophysiological evidence of suppression: Search times for a target at a negatively cued location were delayed relative to a target away from the cued location (inverse validity effects). In addition, an event-related potential indicative for suppression (the Distractor Positivity, Pd) was observed following rhythmic but not arrhythmic stimulation, indicating that suppression was boosted by the stimulation. This was also echoed in higher spectral power and intertrial phase coherence of EEG at rhythmically versus arrhythmically stimulated electrode sites, albeit only at the second harmonic (20 Hz), but not at the stimulation frequency. In addition, inverse validity effects were not modulated by rhythmic entrainment congruent with the cue side. Hence, we propose that rhythmic visual stimulation in the alpha range could support suppression, though behavioral evidence remains elusive, in contrast to electrophysiological findings., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2024 Szaszkó, Habeler, Forstinger, Pomper, Scheftner, Stolte, Grüner and Ansorge.)

Simulation is a crucial tool for the evaluation and comparison of statistical methods. How to design fair and neutral simulation studies is therefore of great interest for both researchers developing new methods and practitioners confronted with the choice of the most suitable method. The term simulation usually refers to parametric simulation, that is, computer experiments using artificial data made up of pseudo-random numbers. Plasmode simulation, that is, computer experiments using the combination of resampling feature data from a real-life dataset and generating the target variable with a known user-selected outcome-generating model, is an alternative that is often claimed to produce more realistic data. We compare parametric and Plasmode simulation for the example of estimating the mean squared error (MSE) of the least squares estimator (LSE) in linear regression. If the true underlying data-generating process (DGP) and the outcome-generating model (OGM) were known, parametric simulation would obviously be the best choice in terms of estimating the MSE well. However, in reality, both are usually unknown, so researchers have to make assumptions: in Plasmode simulation studies for the OGM, in parametric simulation for both DGP and OGM. Most likely, these assumptions do not exactly reflect the truth. Here, we aim to find out how assumptions deviating from the true DGP and the true OGM affect the performance of parametric and Plasmode simulations in the context of MSE estimation for the LSE and in which situations which simulation type is preferable. Our results suggest that the preferable simulation method depends on many factors, including the number of features, and on how and to what extent the assumptions of a parametric simulation differ from the true DGP. Also, the resampling strategy used for Plasmode influences the results. In particular, subsampling with a small sampling proportion can be recommended., Competing Interests: The authors have declared that no competing interests exist., (Copyright: © 2024 Stolte et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.)

Vapor sensors with both high sensitivity and broad detection range are technically challenging yet highly desirable for widespread chemical sensing applications in diverse environments. Generally, an increased surface-to-volume ratio can effectively enhance the sensitivity to low concentrations, but often with the trade-off of a constrained sensing range. Here, an approach is demonstrated for NH 3 sensor arrays with an unprecedentedly broad sensing range by introducing controllable steps on the surface of an n-type single crystal. Step edges, serving as adsorption sites with electron-deficient properties, are well-defined, discrete, and electronically active. NH 3 molecules selectively adsorb at the step edges and nearly eliminate known trap-like character, which is demonstrated by surface potential imaging. Consequently, the strategy can significantly boost the sensitivity of two-terminal NH 3 resistance sensors on thin crystals with a few steps while simultaneously enhancing the tolerance on thick crystals with dense steps. Incorporation of these crystals into parallel sensor arrays results in ppb-to-% level detection range and a convenient linear relation between sheet conductance and semi-log NH 3 concentration, allowing for the precise localization of vapor leakage. In general, the results suggest new opportunities for defect engineering of organic semiconductor crystal surfaces for purposeful vapor or chemical sensing., (© 2024 The Authors. Advanced Science published by Wiley‐VCH GmbH.)

Past research suggests a continuity between perception and memory, as reflected in influences of orienting of spatial attention by cues presented after a visual target offset (post-target cues) on target perception. Conducting two experiments, we tested and confirmed this claim. Our study revealed an elevated reliance on post-target cues for target detection with diminishing target visibility, leading to better performance in validly versus invalidly cued trials, indicative of contrast gain. We demonstrated this post-target cueing impact on target perception without a postcue response prompt, meaning that our results truly reflected a continuity between perception and memory rather than a task-specific impact of having to memorize the target due to a response prompt. While previous studies found an improvement in accuracy through valid compared to invalid cues using liminal targets, in Experiment 1, we further showed an influence of attention on participants' response time by the post-target cues with cues presented away from a clearly visible target. This suggests that visual interactions at the target location provided no better explanation of post-target cueing effects. Our results generalize prior research with liminal targets and confirm the view of a perception-memory continuum so that visual target processing is not shielded against visuospatial orienting of attention elicited by events following the offset of the visual target.

In the current study, we used abrupt-onset distractors similar and dissimilar in luminance to the target of a smooth pursuit eye-movement to test if abrupt-onset distractors capture attention in a top-down or bottom-up fashion while the eyes track a moving object. Abrupt onset distractors were presented at different positions relative to the current position of a pursuit target during the closed-loop phase of smooth pursuit. Across experiments, we varied the duration of the distractors, their motion direction, and task-relevance. We found that abrupt-onset distractors decreased the gain of horizontally directed smooth-pursuit eye-movements. This effect, however, was independent of the similarity in luminance between distractor and target. In addition, distracting effects on horizontal gain were the same, regardless of the exact duration and position of the distractors, suggesting that capture was relatively unspecific and short-lived (Experiments 1 and 2). This was different with distractors moving in a vertical direction, perpendicular to the horizontally moving target. In line with past findings, these distractors caused suppression of vertical gain (Experiment 3). Finally, making distractors task-relevant by asking observers to report distractor positions increased the pursuit gain effect of the distractors. This effect was also independent of target-distractor similarity (Experiment 4). In conclusion, the results suggest that a strong location signal exerted by the pursuit targets led to very brief and largely location-unspecific interference through the abrupt onsets and that this interference was bottom-up, implying that the control of smooth pursuit was independent of other target features besides its motion signal., (© 2023 The Authors. Psychophysiology published by Wiley Periodicals LLC on behalf of Society for Psychophysiological Research.)

Self-assembly versus complexation with polycyclic aromatic hydrocarbon (PAH) guest molecules is studied for a series of perylene bisimides (PBIs). Bulky imide substituents at the PBI guide their self-assembly into dimer aggregates with null-type exciton coupling. Host-guest titration experiments with perylene and triphenylene PAHs afford 1 : 1 and 1 : 2 complexes whose properties are studied by single crystal X-ray analysis and UV/Vis and fluorescence spectroscopy.

Five chiral squaraine dimers were synthesized by fusing chiral indolenine semisquaraines with three different benzobisthiazole bridges. The thereby created squaraine dimers show a strong splitting of the lowest energy absorption bands caused by exciton coupling. The intensities of the two exciton transitions and the energetic splitting depend on the angle of the two squaraine moieties within the chromophore dimer. The electric circular dichroism spectra of the dimers show intense Cotton effects whose sign depends on the used squaraine chromophores. Sizable anisotropies g abs of up to 2.6 × 10 -3 could be obtained. TD-DFT calculations were used to partition the rotational strength into the three Rosenfeld terms where the electric-magnetic coupling turned out to be the dominant contribution while the exciton chirality term is much smaller. This is because the chromophore dimers are essentially planar but the angle between the electric transition dipole moment of one squaraine and the magnetic transition dipole moment of the other squaraine strongly deviates from 90°, which makes the dot product between the two moment vectors and, thus, the rotational strength substantial.

The Sensory Gating Inventory (SGI) is an established self-report questionnaire that is used to assess the capacity for filtering redundant or irrelevant environmental stimuli. Translation and cross-cultural validation of the SGI are necessary to make this tool available to Dutch speaking populations. This study, therefore, aimed to design and validate a Dutch Sensory Gating Inventory (D-SGI). To this end, a forward-backward translation was performed and 469 native Dutch speakers filled in the questionnaire. A confirmatory factor analysis assessed the psychometric properties of the D-SGI. Additionally, test-retest reliability was measured. Results confirmed satisfactory similarity between the original English SGI and the D-SGI in terms of psychometric properties for the factor structure. Internal consistency and discriminant validity were also satisfactory. Overall test-retest reliability was excellent (ICC = 0.91, p  < 0.001, 95% CI [0.87-0.93]). These findings confirm that the D-SGI is a psychometrically sound self-report measure that allows assessing the phenomenological dimensions of sensory gating in Dutch. Moreover, the D-SGI is publicly available. This establishes the D-SGI as a new tool for the assessment of sensory gating dimensions in general- and clinical Dutch speaking populations.

Chiral polycyclic aromatic hydrocarbons can be tailored for next-generation photonic materials by carefully designing their molecular as well as supramolecular architectures. Hence, excitonic coupling can boost the chiroptical response in extended aggregates but is still challenging to achieve by pure self-assembly. Whereas most reports on these potential materials cover the UV and visible spectral range, systems in the near infrared (NIR) are underdeveloped. We report a new quaterrylene bisimide derivative with a conformationally stable twisted π-backbone enabled by the sterical congestion of a fourfold bay -arylation. Rendering the π-subplanes accessible by small imide substituents allows for a slip-stacked chiral arrangement by kinetic self-assembly in low polarity solvents. The well dispersed solid-state aggregate reveals a sharp optical signature of strong J-type excitonic coupling in both absorption (897 nm) and emission (912 nm) far in the NIR region and reaches absorption dissymmetry factors up to 1.1 × 10 -2 . The structural elucidation was achieved by atomic force microscopy and single-crystal X-ray analysis which we combined to derive a structural model of a fourfold stranded enantiopure superhelix. We could deduce that the role of phenyl substituents is not only granting stable axial chirality but also guiding the chromophore into a chiral supramolecular arrangement needed for strong excitonic chirality.

Two [ n ]heliceno-bis(naphthalimides) 1 and 2 ( n = 5 and 6, respectively) where two electron-accepting naphthalimide moieties are attached at both ends of helicene core were synthesized by effective two-step strategy, and their enantiomers could be resolved by chiral stationary-phase high-performance liquid chromatography (HPLC). The single-crystal X-ray diffraction analysis of enantiopure fractions of 1 and 2 confirmed their helical structure, and together with experimental and calculated circular dichroism (CD) spectra, the absolute configuration was unambiguously assigned. Both 1 and 2 exhibit high molar extinction coefficients for the S 0 -S 1 transition and high fluorescence quantum yields (73% for 1 and 69% for 2 ), both being outstanding for helicene derivatives. The red circularly polarized luminescence (CPL) emission up to 615 nm for 2 with CPL brightness ( B ) up to 66.5 M CPL ) up to 66.5 M -1 cm -1 demonstrates its potential for applications in chiral optoelectronics. Time-dependent density functional theory (TD-DFT) calculations unambiguously showed that the large transition magnetic dipole moment | m | of 2 is responsible for its high absorbance dissymmetry ( g abs ) and luminescence dissymmetry ( g lum ) factor.

Perylene bisimide (PBI) dyes are known as red, maroon and black pigments, whose colors depend on the close π-π stacking arrangement. However, contrary to the luminescent monomers, deep-red and black PBI pigments are commonly non- or only weakly fluorescent due to (multiple) quenching pathways. Here, we introduce N-alkoxybenzyl substituted PBIs that contain close π stacking arrangement (exhibiting d π-π ≈ 3.5 Å, and longitudinal and transversal displacements of 3.1 Å and 1.3 Å); however, they afford deep-red emitters with solid-state fluorescence quantum yields (Φ F ) of up to 60%. Systematic photophysical and computational studies in solution and in the solid state reveal a sensitive interconversion of the PBI-centred locally excited state and a charge transfer state, which depends on the dihedral angle (θ) between the benzyl and alkoxy groups. This effectively controls the emission process, and enables high Φ F by circumventing the common quenching pathways commonly observed for perylene black analogues., (© 2023. The Author(s).)

Heavy-atom-containing clusters, nanocrystals, and other semiconductors can sensitize the triplet states of their surface-bonded chromophores, but the energy loss, such as nonradiative deactivation, often prevents the synergistic light emission in their solid-state coassemblies. Cocrystallization allows new combinations of molecules with complementary properties for achieving functionalities not available in single components. Here, the cocrystal formation that employs platinum(II) acetylacetonate (Pt(acac) 2 ) as a triplet sensitizer and electron-deficient 1,4,5,8-naphthalene diimides (NDIs) as organic phosphors is reported. The hybrid cocrystals exhibit room-temperature phosphorescence confined in the low-lying, long-lived triplet state of NDIs with photoluminescence (PL) quantum yield (Φ PL ) exceeding 25% and a phosphorescence lifetime (τ Ph ) of 156 µs. This remarkable PL property benefits from the noncovalent electronic and spin-orbital coupling between the constituents., (© 2022 The Authors. Advanced Materials published by Wiley-VCH GmbH.)

Human retina- and brain-inspired optoelectronic synapses, which integrate light detection and signal memory functions for data processing, have significant interest because of their potential applications for artificial vision technology. In nature, many animals such as mantis shrimp use polarized light information as well as scalar information including wavelength and intensity; however, a spectropolarimetric organic optoelectronic synapse has been seldom investigated. Herein, we report an organic synaptic phototransistor, consisting of a charge trapping liquid-crystalline perylene bisimide J-aggregate and a charge transporting crystalline dichlorinated naphthalene diimide, that can detect both wavelength and polarization information. The device shows persistent positive and negative photocurrents under low and high voltage conditions, respectively. Furthermore, the aligned organic heterostructure in the thin-film enables linearly polarized light to be absorbed with a dichroic ratio of 1.4 and 3.7 under transverse polarized blue and red light illumination, respectively. These features allow polarized light sensitive postsynaptic functions in the device. Consequently, a simple polarization imaging sensor array is successfully demonstrated using photonic synapses, which suggests that a supramolecular material is an important candidate for the development of spectropolarimetric neuromorphic vision systems.

Yamamoto homocoupling of two chiral oxindoles led to the atropo-diastereoselective formation of an axially chiral oxindole dimer. This building block served as the starting material for the syntheses of axially chiral squaraine and merocyanine chromophore dimers. These dimers show pronounced chiroptical properties, this is, outstandingly high ECD signals (Δ ε up to ca. 1500 M -1 cm -1 ) as a couplet with positive Cotton effect for the P -configuration around the biaryl axis and a negative Cotton effect for the M -configuration. All investigated dimers also exhibit pronounced circularly polarised emission with anisotropy values of ca. 10 -3 cgs. Time-dependent density functional calculations were used to analyse the three contributions (local one electron, electric-magnetic coupling, and exciton coupling) to the rotational strength applying the Rosenfeld equation to excitonically coupled chromophores. While the exciton coupling term proves to be the dominant one, the electric-magnetic coupling possesses the same sign and adds significantly to the total rotational strength owing to a favourable geometric arrangement of the two chromophores within the dimer., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

A new class of perylene bisimide (PBI) derivatives is introduced by bridging 1,12- and 1,6,7,12-hydroxy functionalized bay positions with oxygen-carbon-oxygen linker(s). This functionalization rigidifies the inherently twisted bay-substituted perylene core to afford dyes of high stability and solubility that are characterized by vibronically well-resolved absorption and fluorescence spectra and intense yellow emission with quantum yields close to 100%.

Previous research on ADHD and ASD has mainly focused on the deficits associated with these conditions, but there is also evidence for strengths. Unfortunately, our understanding of potential strengths in neurodevelopmental conditions is limited. One particular strength, creativity, has been associated with both ADHD and ASD. However, the distinct presentations of both conditions beg the question whether ADHD and ASD associate with the same or different aspects of creativity. Therefore, the current study investigated the links between ADHD and ASD symptoms, creative thinking abilities, and creative achievements. To investigate the spectrum of ADHD and ASD symptoms, self-reported ADHD and ASD symptoms, convergent (Remote Associations Test) and divergent thinking (Alternative Uses Task) and creative achievements (Creative Achievement Questionnaire) were assessed in a self-reportedly healthy sample of adults ( n = 470). We performed correlation analysis to investigate the relation between ADHD/ASD symptoms and creativity measures. In a second phase of analysis, data from an adult ADHD case-control study ( n = 151) were added to investigate the association between ADHD symptoms and divergent thinking in individuals with and without a diagnosis of ADHD. Our analysis revealed that having more ADHD symptoms in the general population was associated with higher scores on all the outcome measures for divergent thinking (fluency, flexibility, and originality), but not for convergent thinking. Individuals with an ADHD diagnosis in the case-control sample also scored higher on measures of divergent thinking. Combining data of the population based and case-control studies showed that ADHD symptoms predict divergent thinking up to a certain level of symptoms. No significant associations were found between the total number of ASD symptoms and any of the creativity measures. However, explorative analyses showed interesting links between the ASD subdomains of problems with imagination and symptoms that relate to social difficulties. Our findings showed a link between ADHD symptoms and divergent thinking abilities that plateaus in the clinical spectrum of symptoms. For ASD symptoms, no relation was found with creativity measures. Increasing the knowledge about positive phenotypes associated with neurodevelopmental conditions and their symptom dimensions might aid psychoeducation, decrease stigmatization and improve quality of life of individuals living with such conditions., Competing Interests: BF has received educational speaking fees from Medice. The remaining authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2022 Stolte, Trindade-Pons, Vlaming, Jakobi, Franke, Kroesbergen, Baas and Hoogman.)

Graphene nanoribbons (GNRs) have the potential for next-generation functional devices. So far, GNRs with defined stereochemistry are rarely reported in literature and their optical response is usually bound to the ultraviolet or visible spectral region, while covering the near-infrared (NIR) regime is still challenging. Herein, we report two novel quaterrylene bisimides with either one- or twofold-twisted π-backbones enabled by the steric congestion of a fourfold bay arylation leading to an end-to-end twist of up to 76°. The strong interlocking effect of the π-stacked aryl substituents introduces a rigidification of the chromophore unambiguously proven by single-crystal X-ray analysis. This leads to unexpectedly strong NIR emissions at 862 and 903 nm with quantum yields of 1.5 and 0.9%, respectively, further ensuring high solubility as well as resolvable and highly stable atropo-enantiomers. Circular dichroism spectroscopy of these enantiopure chiral compounds reveals a strong Cotton effect Δε of up to 67 M -1 cm -1 centered far in the NIR region at 849 nm.

The current study investigated whether lower sensory and sensorimotor gating were related to higher levels of creativity and/or attentional difficulties in a natural population of primary school children (9- to 13-year-old). Gating abilities were measured with P50 suppression and prepulse inhibition of the startle reflex (PPI). The final sample included 65 participants in the P50 analyses and 37 participants in the PPI analyses. Our results showed that children with a high P50 amplitude to testing stimuli scored significantly higher on the divergent outcome measures of fluency and flexibility but not originality compared to children with a lower amplitude. No significant differences were found on any of the creativity measures when the sample was split on average PPI parameters. No significant differences in attention, as measured with a parent questionnaire, were found between children with low or high levels of sensory or sensorimotor gating. The data suggest that quantitative, but not qualitative measures of divergent thinking benefit from lower psychophysiological gating and that attentional difficulties stem from specific instead of general gating deficits. Future studies should take the effect of controlled attention into consideration., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2022 Stolte, Oranje, Van Luit and Kroesbergen.)

Dye-dye interactions affect the optical and electronic properties in organic semiconductor films of light harvesting and detecting optoelectronic applications. This review elaborates how to tailor these properties of organic semiconductors for organic solar cells (OSCs) and organic photodiodes (OPDs). While these devices rely on similar materials, the demands for their optical properties are rather different, the former requiring a broad absorption spectrum spanning from the UV over visible up to the near-infrared region and the latter an ultra-narrow absorption spectrum at a specific, targeted wavelength. In order to design organic semiconductors satisfying these demands, fundamental insights on the relationship of optical properties are provided depending on molecular packing arrangement and the resultant electronic coupling thereof. Based on recent advancements in the theoretical understanding of intermolecular interactions between slip-stacked dyes, distinguishing classical J-aggregates with predominant long-range Coulomb coupling from charge transfer (CT)-mediated or -coupled J-aggregates, whose red-shifts are primarily governed by short-range orbital interactions, is suggested. Within this framework, the relationship between aggregate structure and functional properties of representative classes of dye aggregates is analyzed for the most advanced OSCs and wavelength-selective OPDs, providing important insights into the rational design of thin-film optoelectronic materials., (© 2021 The Authors. Advanced Materials published by Wiley-VCH GmbH.)

A series of donor-acceptor (D-A) macrocyclic dyads consisting of an electron-poor perylene bisimide (PBI) π-scaffold bridged with electron-rich α-oligothiophenes bearing four, five, six and seven thiophene units between the two phenyl-imide substituents has been synthesized and characterized by steady-state UV/Vis absorption and fluorescence spectroscopy, cyclic and differential pulse voltammetry as well as transient absorption spectroscopy. Tying the oligothiophene strands in a conformationally fixed macrocyclic arrangement leads to a more rigid π-scaffold with vibronic fine structure in the respective absorption spectra. Electrochemical analysis disclosed charged state properties in solution which are strongly dependent on the degree of rigidification within the individual macrocycle. Investigation of the excited state dynamics revealed an oligothiophene bridge size-dependent fast charge transfer process for the macrocyclic dyads upon PBI subunit excitation., (© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)