Nanofibers of Hydrogen-Bonded Two-Component Gel with Closely Connected p- and n‑Channels and Photoinduced Electron Transfer

An D–A–D gelator (DTCQ) was designed and synthesized using 2,3-dimethyl-5,8-di­(thiophen-2-yl)­quinoxaline and N-alkyl 3-aminocarbazole units as acceptor and donor, respectively, which were linked by a single bond. The compound could gelate several solvents, such as benzyl alcohol, aniline, acetophenone, and o-dichlorobenzene, as well as self-assemble into one-dimensional (1D) nanofibers in gel phase. The absorption and infrared spectra of the gels indicated that π–π interactions between aromatic moieties, intermolecular hydrogen bonds between amide units, and van der Waals forces were the driving forces for the formation of 1D self-assemblies and gel. DTCQ gel was red and emits red fluorescence because it has a strong absorption band at 487 nm and an emissive band at 620 nm. Moreover, DTCQ and a fullerene carboxylic acid formed two-component gel, in which the two compounds developed a hydrogen bond complex and self-assembled into 1D nanofibers with closely connected p- and n-channels. The nanofibrous xerogel film can rapidly generate a photocurrent under visible-light radiation through electron transfer from the gelator to fullerene, and then, the excellent exciton separation and charge transfer to two electrodes.