Luminescent Organic 1D Nanomaterials Based on Bis(β‐diketone)carbazole Derivatives

Abstract

A series of new triphenylamine-functionalized bis(β-diketone)s bridged by a carbazole (CnBDKC, n=1, 4, 8, 16) with twisted intramolecular charge-transfer emission in polar solvents has been synthesized. The length of the carbon chains has a significant effect on the self-assembling properties of the compounds. Well-defined 1D nanowires were easily generated from C1BDKC with a methyl group by a reprecipitation approach directed by π-stacking interaction, and the molecules packed into J-aggregates in the nanowires. In addition, 1D nanofibers based on C16BDKC bearing a long hexadecyl chain were prepared through the organogelation process, and H-aggregates were formed driven by the synergistic effect of π-stacking interaction and van der Waals force in the gel phase. C4BDKC and C8BDKC containing butyl and octyl side chains, respectively, cannot arrange into dispersed nanostructures, probably because π-π interaction between conjugated moieties might be disturbed by the interaction between the side chains, which is, however, not strong enough to dominate the self-assembling process. Notably, the nanowires based on C1BDKC and the gel nanofibers from C16BDKC can emit strong green light under irradiation, which suggests that these 1D nanomaterials may have potential applications in emitting materials as well as photonic devices.

Triphenylamine/tetrazine based π-conjugated systems as molecular donors for organic solar cells

“…[25][26][27][28][29][30][31][32][33][34] Very recently, polymers containing s-tetrazine have been used in organic photovoltaic (OPV) cells [35][36][37][38][39] and there is one example of transistor based on a tetrazine-naphthalene diimide system. 40 Triphenylamine (TPA) is a well-known electron-donor unit, extensively investigated in diverse fields including electrochromism, [41][42][43][44][45][46][47] organic electronics [48][49][50][51][52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67] or two-photon absorption. [68][69][70][71][72][73]…”

Branched benzothiadiazole-cored oligomers with terminal carbazoles: Synthesis and fluorescence probing nitroaromatics

“…However, the maximal emission of 1 redshifted significantly with increasing the polarities of the solvents, for example, it appeared at 594 nm in CCl 4 and shifted to 637 nm in chloroform. The increase of Stokes shifts (Tables S2eS3) with the increasing polarity of the solvents pointed to a large solvent relaxation and strong stabilization of the excited state in the polar solvents [21]. Meanwhile, the emission band became broader in the solvents with high polarities.…”

Highly Luminescent Organic Nanorods from Air Oxidation of para‐Substituted Anilines for Freestanding Deep‐Red Color Filters

“…Yet, luminescent organic nanostructures have superior competitiveness compared to other nanostructures in terms of easy fabrication, flexibility, environmental stability, and low cost. Especially, luminescent 1D organic nanostructures based on organic π‐conjugated molecules take rising attention as building blocks for several unique functional devices such as lasers, waveguides, solar cells, and field‐effect transistors . Although several success in constructing luminescent 1D organic materials by self‐assembly or self‐organization were achieved, the synthesis of those materials starts from preparing luminescent organic molecules, which are produced from over several organic reaction and purification steps, requiring significant time, skill, and attention.…”