Search

New difluoroboron β-carbonyl cyclic ketonate complexes CnB (n = 2, 16), in which carbazole was linked to difluoroboron β-diketonate directly, and DCnB (n = 2, 16), where two terminal carbazole units were bridged by vinyl groups to link to difluoroboron β-diketonate core, were synthesized. They exhibited reversible mechanofluorochromic (MFC) behavior under grinding/fuming or heating treatment. Particularly, the emission of DC2B and DC16B emerged in the range of 650–850 nm in the solid-state. They gave red and rose-red luminescence in the as-synthesized crystals and in the ground powders, respectively, during MFC processes. Such MFC materials emitting NIR (near-infrared) light were seldom reported. In addition, compared with C2B , C16B showed high-contrast mechanofluorochromism because the long alkyl chain might decrease the strength of π-π interactions in the as-synthesized crystals, leading to the emission appeared at the high-energy region (483 nm). The disassembling of parts of π-aggregates and the improvement of the molecular planarity led to red-shift of the emission (509 nm) upon grinding. [ABSTRACT FROM AUTHOR]

Novel luminescent organogelators based on nucleoside functionalized with carbazole (UC8, UC12 and UC16) were designed and synthesized. Their gelation ability was tested and it was found that both UC12 and UC16 could form stable organogels in toluene/petroleum ether. The UV-vis absorption, fluorescence emission and IR spectral changes during the gelation of UC12 proved that the self-assembly was driven by H- bonding. The morphology of the xerogel UC16 obtained from toluene/petroleum ether (v/v = 1/1) displayed tough rod-like microstructures, and 3D networks formed from lots of nanofibers were observed for the xerogel UC16 obtained from toluene/petroleum ether (v/v = 2/1). It was interesting that the obtained organogels emitting blue light could be destroyed by the addition of F-, accompanied with the declining the emission intensity. Therefore, these organogels could be used as sensory materials to recognize F-. [ABSTRACT FROM AUTHOR]

We have synthesized a series of new β-iminoenolates and their corresponding difluoroboron complexes without any traditional gelation moieties, and some of them were able to gelatinize organic solvents. It was found that the presence of halogen atoms as substituents had a significant effect on gelation ability. In particular, bromo-containing compounds 4 A and 4 B exhibited excellent gelation abilities compared with other halogen-substituted gelators. By analyses of the single-crystal structure, the PXRD pattern of the xerogel, and electronic spectral changes during gelation, we deemed that π-π, C−H⋅⋅⋅F, and C−H⋅⋅⋅Br interactions were the driving forces for the gelation of 4 B. Interestingly, ( Z)-1-(4-bromophenyl)-2-(3-methylpyrazin-2-yl)ethen-1-ol ( 8 A), prepared in this work, is the lowest-molecular-weight organogelator to have been reported. It should be noted that although β-iminoenolates 3 A- 5 A are nonemissive in solution, they emit strong yellow light in organogels, which suggests aggregation-induced emissive activity, whereas the difluoroboron complexes 3 B- 5 B show strong fluorescence in solutions, organogels, and xerogel-based films. Moreover, we found that the emission of 4 B in a nanofiber-based film could be quenched significantly upon exposure to gaseous trifluoroacetic acid and that the decay time and detection limit were 0.5 s and 0.17 ppm, respectively. Thus, through this work we have provided a new strategy for the design of nontraditional π gelators by introducing halogen atoms into π-conjugated systems with moderate polarities. [ABSTRACT FROM AUTHOR]

New difluoroboron β-diketonate complexes functionalized with tert -butyl carbazole and carbazole ( TCBM and CBM ) have been synthesized, and they give strong emission in solid states with the fluorescence quantum yields of 0.63 and 0.99, respectively. Reversible mechanofluorochromic behaviors of TCBM and CBM are realized upon the treatment of grinding/fuming with CH 2 Cl 2 . Interestingly, the emitting colors of the annealed samples gained from the ground powders of TCBM depend on the heating temperature, and change from orange to yellow, yellowish green, and green with increasing temperature. The X-ray diffraction patterns illustrate that the transformation processes from crystalline structure to partial destroyed crystalline structure, till to amorphous state lead to the multi-color solid-state luminescence during thermofluorochromism. We deduced that tert -butyl can lead to the incompact packing of luminophores, which is more sensitive to external stimuli, so that multi-color solid-state luminescence can be afforded during mechanofluorochromic and thermofluorochromic processes. [ABSTRACT FROM AUTHOR]

Nanofibers based on phenanthroimidazole derivatives PCC, PDC, and PSC were fabricated by organogelation processes, and their fluorescence sensory properties towards acid were investigated. It was found that the emission of PCC in the nanofiber-based film could be quenched significantly upon exposure to gaseous TFA due to the formation of protonated PCC, in which ICT (intramolecular charge transfer) would occur. On the other hand, TFA vapor led to the emitting colors of PDC and PSC in the nanofiber-based films to turn to yellow and green from sky blue and blue, respectively. Additionally, we found that the decay times of PCC were 0.1 s and 1.9 s in probing the saturated vapor of TFA in nanofiber-based film and in spin-coated film, respectively. The results suggested that the high surface-to-volume ratio and large interspace in the nanofiber-based networks favored the enhanced adsorption, accumulation, and diffusion of gaseous molecules, resulting in such a high performance. [ABSTRACT FROM AUTHOR]

4-(Carbazol-9-yl)benzaldehyde could emit yellow RTP, which could last for 3 s because of efficient intersystem crossing. Moreover, multicolor luminescent switches could be realized by simply applying a mechanical force stimulus. [ABSTRACT FROM AUTHOR]

New triphenylvinyl substituted carbazole derivatives TPEICE , TPEC and TPECBr have been synthesized. They could self-assemble into nanofibers via organogelation processes in some organic solvents. Notably, the obtained xerogel-based films could emit strong fluorescence although the three compounds were non-emissive in solutions, indicating AIE in gel phases. The emission of TPEICE and TPEC in xerogel-based films could be quenched significantly upon exposed to gaseous DNT and TNT, while TPECBr could not sense nitro compounds on account of its poor electron donating ability. We also found that reversibility of the fluorescence response of TPEC was better than TPEICE because the photo-induced electron transfer would happen during the recognition of nitroaromatics for TPEICE and TPEC , except for the formation of charge–transfer complex between TPEICE and nitro compounds. Therefore, the different fluorescence response behaviors of TPEICE , TPEC and TPECBr towards nitroaromatics were resulted from their different electron donating abilities. [ABSTRACT FROM AUTHOR]