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Five new copolymers based on the anthanthrone moiety were synthesized using Stille coupling. The anthanthrone unit was coupled with two electron-rich units (thiophene and carbazole) and three electron-poor units (thienopyrroledione, diketopyrrolopyrrole, and benzothiadiazole). The optoelectronics properties of the polymers were investigated and suggest that the anthanthrone moiety dictates the electronic properties of the materials with little regards to the nature of the comonomers. Fluoride-promoted photoinduced electron transfer on anthanthrone derivatives yielded to radical anion species that can be reversibly oxidized to the neutral form by exposure to air.

Six anthanthrene-based conjugated polymers with either electron-rich or electron-poor units were synthesized and characterized. All polymers exhibit optical absorption in the visible region owing to their extended conjugation. Experimental data and computational results indicate that the comonomer attached to the anthanthrene unit has only little effect on the electronic properties of the polymers.

Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1–P5) based on poly[(arylene ethynylene)-alt-(arylene vinylene)]s backbone (−Ph–C≡C–Anth–C≡C–Ph–CH=CH–Ph–CH=CH−)n. During the synthesis of P1–P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2-ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones containing carbonyl groups were converted to anthanthrene containing alkyloxy substituents) were soluble. The photophysical, electrochemical, electroluminescent and photovoltaic properties of P1–P3 are reported, compared and discussed with respect to the effects of side chains.

The design of advanced new generation conjugated materials with improved properties for photovoltaic applications has been the focus of research in recent years. This work reports on novel anthanthrone/anthracene and anthanthrene/anthracene co-polymers as p-type conjugated semiconductors in organic photovoltaics. The presence of anthracene component with the grafted alkyloxy chains enhanced the solubility and process-ability of the co-polymers. The photophysical and photovoltaic parameters greatly depend on ratio of components of the co-polymers and nature of the grafted chains. Devices using the blends of SV15 and PCBM in 1:2 ratio gave $J_{\mathrm{s}\mathrm{c}}$ 3.97 mA/cm2 and higb $V_{oc}$ 0.92 V with efficiency 1.7%.

Synthetic efforts toward the preparation of rotaxane precursors based on phenylacetylene macrocycles (PAM) are described. The aim of this study was to determine the optimal structural parameters to prepare high-molecular-weight rotaxane precursors through a strategy involving two Sonogashira couplings to attach bulky blockers on the PAM core. PAMs with different sizes and functions were prepared and coupled to different blockers to assess whether or not the resulting structure adopts a rotaxane-like conformation in which the rigid rod forms after the Sonogashira coupling threads through the PAM.

A new soluble C 60 derivative bearing a diketopyrrolopyrrole (DPP) moiety has been synthesized by ethynylation reaction. Characterization by UV–visible spectrophotometry and cyclic voltammetry has been performed in order to study the influence of the DPP moiety on electronic and optical properties of the fullerene. Moreover, DFT calculations have been conducted on the derivative and its precursor in order to correlate the orbital geometry with experimental data.