Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 10, Pages 4076-4080Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00364
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Funding
- Wesco Scientific Promotion Foundation
- MEXT (Ministry of Education, Culture, Sports, Science, and Technology)
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We designed anthracene bisimide (ABI) derivatives having two triphenylamine (TPA) groups as donor units at the 9,10-positions to form a novel pi-conjugated donor-acceptor system. These compounds and their analogues with ethynylene linkers were synthesized by Suzuki-Miyaura and Sonogashira coupling reactions, respectively. In UV-vis spectra, the linker-free derivatives showed broad absorption bands arising from intramolecular charge-transfer interactions. Introducing ethynylene linkers resulted in a considerable red shift of the absorption bands. In fluorescence spectra, the ethynylene derivatives showed intense emission bands at 600-650 nm. Their photophysical and electrochemical properties were compared with those of the corresponding mono TPA derivatives on the basis of theoretical calculations and cyclic voltammetry to evaluate the intramolecular electronic interactions between the donor and acceptor units.
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