X-ray structure analysis of compound 13.
1099-0690/asset/2046_left.gif?v=1&s=0ec9ed8843eb5403f667ad940f5a1c68cb5ef011)
1099-0690/asset/2046_right.gif?v=1&s=b2caf576ff74b55a6a4748bd86a910901b664c52)
Full Paper
Synthesis and Electronic Properties of 3-Acceptor-Substituted and 3,7-Bisacceptor-Substituted Phenothiazines
Article first published online: 10 NOV 2005
DOI: 10.1002/ejoc.200500539
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Sailer, M., Nonnenmacher, M., Oeser, T. and Müller, T. J. J. (2006), Synthesis and Electronic Properties of 3-Acceptor-Substituted and 3,7-Bisacceptor-Substituted Phenothiazines. Eur. J. Org. Chem., 2006: 423–435. doi: 10.1002/ejoc.200500539
Publication History
- Issue published online: 2 JAN 2006
- Article first published online: 10 NOV 2005
- Manuscript Received: 15 JUL 2005
- Abstract
- Article
- References
- Cited By
Keywords:
- Catalysis;
- Cyclic voltammetry;
- Fluorescence;
- Heterocycles;
- Substituent effects
Abstract
3-Acceptor-substituted and 3,7-bisacceptor-substituted phenothiazines can be synthesized in moderate to excellent yields through Suzuki cross-coupling reactions between phenothiazin-3-yl pinacolyl boronates or phenothiazin-3,7-diyl bis(pinacolyl boronates) and electron-deficient (hetero)aryl halides. The electronic properties of (hetero)aryl-substituted N-methyl phenothiazines (UV/Vis absorption, fluorescence, redox potentials) can be correlated with the computed energies of the frontier molecular orbitals. Nitro-substituted derivatives reveal electronically amphoteric behavior, displaying both reversible oxidations and reversible reductions. X-ray structure analysis of the phenothiazinyl p-(2,5-dinitro)phenylene-bridged dyad 13 revealed donor–acceptor interactions between the molecules. Pyridyl and pyrimidyl derivatives fluoresce with quantum yields (Φf) of up to 49 % and can be regarded as redox-active fluorophores. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)