期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2006, 期 2, 页码 423-435出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200500539
关键词
catalysis; cyclic voltammetry; fluorescence; heterocycles; substituent effects
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 (phi(f)) of up to 49% and can be regarded as redox-active fluorophores. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
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