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Structure-Dependent cis/ trans Isomerization of Tetraphenylethene Derivatives: Consequences for Aggregation-Induced Emission.
- Source :
-
Angewandte Chemie . 5/17/2016, Vol. 128 Issue 21, p6300-6304. 5p. - Publication Year :
- 2016
-
Abstract
- The isomerization and optical properties of the cis and trans isomers of tetraphenylethene (TPE) derivatives with aggregation-induced emission (AIEgens) have been sparsely explored. We have now observed the tautomerization-induced isomerization of a hydroxy-substituted derivative, TPETH-OH, under acidic but not under basic conditions. Replacing the proton of the hydroxy group in TPETH-OH with an alkyl group leads to the formation of TPETH-MAL, for which the pure cis and trans isomers were obtained and characterized by HPLC analysis and NMR spectroscopy. Importantly, cis-TPETH-MAL emits yellow fluorescence in DMSO at −20 °C whereas trans-TPETH-MAL shows red fluorescence under the same conditions. Moreover, the geometry of cis- and trans-TPETH-MAL remains unchanged when they undergo thiol-ene reactions to form cis- and trans-TPETH-cRGD, respectively. Collectively, our findings improve our fundamental understanding of the cis/ trans isomerization and photophysical properties of TPE derivatives, which will guide further AIEgen design for various applications. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 128
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 115296251
- Full Text :
- https://doi.org/10.1002/ange.201600244