首页|Organic dyads and triads based on the triphenylene-rylenediimide couple: Molecular design, self-organization, and photo-physical properties

Organic dyads and triads based on the triphenylene-rylenediimide couple: Molecular design, self-organization, and photo-physical properties

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Liquid-crystalline D-A dyads and A-D-A triads, based on the chemical association of electron-donor (D) triphe-nylene discogens and electron-acceptor (A) perylene/benzoperylene diimides, have been synthesized by the Pd-catalyzed Sonogashira coupling/DBU-promoted cyclization reactions tandem. These molecular heterojunctions spontaneously self-organize into columnar hexagonal (Colhex) or/and rectangular (Col_(rec)) mesophases, over broad temperature ranges including room temperature, with the antagonist moieties segregated into alternated homo-molecular (homolithic) stacks within mixed columns. Their intramolecular electron and energy transfers have been studied by UV/Vis absorption and fluorescence emission spectroscopies. Due to photo-induced electron transfer between donor and acceptor units, fluorescence quenching is systematically observed for all the dyads and triads. This study further reveals that perylenediimide is a stronger electron acceptor than the larger benzoperylenediimide building block. Density function theory calculations of their molecular structures and HOMO-LUMO energy levels and gaps support the experimental results and demonstrate that these donor-acceptor systems have potential applications in various optoelectronic devices.

Molecular heterojunctionDiscotic liquid crystalTriphenylenePerylene bisimideBenzoperylenebisimideHexagonal/rectangular columnar phasePhotoluminescenceElectron donor/acceptorPhoto-induced electron/energy transferDensity function theory calculationOrbital frontiers

Hang Lin、Qiu-Bing Lv、Hai-Feng Wang

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College of Chemistry and Material Science, Sichuan Normal University, Chengdu, 610066, China

2022

10.1016/j.dyepig.2021.109911

Dyes and Pigments

Dyes and Pigments

EISCI
ISSN：0143-7208
年,卷(期)：2022.197
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