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Organic dyads and triads based on the triphenylene-rylenediimide couple: Molecular design, self-organization, and photo-physical properties.
- Source :
-
Dyes & Pigments . Jan2022, Vol. 197, pN.PAG-N.PAG. 1p. - Publication Year :
- 2022
-
Abstract
- Liquid-crystalline D-A dyads and A-D-A triads, based on the chemical association of electron-donor (D) triphenylene 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 (Col hex) 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. • Dyad and triad discotic mesogens were synthesized by Sonogashira coupling/DBU-promoted cyclization reactions tandem. • Fluorescence quenching is observed for all compounds due to photo-induced electron transfer between donors and acceptors. • The compounds exhibit hexagonal and rectangular columnar mesophases over broad temperature ranges. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 01437208
- Volume :
- 197
- Database :
- Academic Search Index
- Journal :
- Dyes & Pigments
- Publication Type :
- Academic Journal
- Accession number :
- 153849608
- Full Text :
- https://doi.org/10.1016/j.dyepig.2021.109911