Journal
NEW JOURNAL OF CHEMISTRY
Volume 39, Issue 11, Pages 8874-8880Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5nj01072a
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Funding
- Natural Science Foundation of Jiangsu Province [BK20150285]
- Natural Science Foundation of Education Department of Jiangsu Province [11KJA430003]
- Natural Science Foundation for colleges and universities in Jiangsu Province [14KJB150024]
- Excellent Innovation Team in Science and Technology of Education Department of Jiangsu Province
- Priority Academic Program Development of Education Department of Jiangsu Province (PAPD)
- Project of Science Technology of Suzhou [SYG201204]
- Key Lab of Advanced Optical Manufacturing Technologies of Jiangsu Province [KJS1102]
- Suzhou University of Science and Technology [XKQ201312]
- Collaborative Innovation Center of Technology and Material of Water Treatment
- [51273141]
- [51303122]
- [21203135]
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Three new donor-p bridge-acceptor (D-p-A) compounds based on triphenylamine-propenone, namely 4-(1-phenylprop-2-en-1-one-3-yl)triphenylamine (PhO-TPA), 4-(1-(pyridin-2-yl)prop-2-en-1-one-3-yl)triphenylamine (PyO-TPA) and 4,4',4 ''-(tri(1-(pyridin-2-yl) prop-2-en-1-one-3-yl)) triphenylamine (TPyO-TPA), were synthesized through an aldol addition reaction. Their intramolecular charge transfer (ICT) and aggregation emission properties as well as packing structures were investigated. All of them show solvent polarity dependent emission. The density function theory calculations reveal that the ICT characteristic of the HOMO-LUMO transition is responsible for the large solvent effect. In aggregates, PhO-TPA and PyO-TPA exhibit aggregation-induced enhanced emission (AIEE). However, TPyO-TPA displays a different fluorescence behavior. Single-crystal analyses of PhO-TPA and PyO-TPA show that the weak intermolecular interactions and the suppression of the ICT state result in the efficient AIEE. The understanding on the AIEE fluorophores together with ICT characteristic will help to develop materials with color tenability, especially the ones with efficient emission in solid states.
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