Remarkable Solvent-Dependent Excited-State Chirality: A Molecular Modulator of Circularly Polarized Luminescence

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• 作者：Richard A. van Delden ; Nina P. M. Huck ; Jacob J. Piet ; John M. Warman ; Stefan C. J. Meskers ; Harry P. J. M. Dekkers ; and Ben L. Feringa
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：December 17, 2003
• 年：2003
• 卷：125
• 期：50
• 页码：15659 - 15665
• 全文大小：158K
• 年卷期：v.125,no.50(December 17, 2003)
• ISSN：1520-5126

文摘

The photochemical control of ground- and excited-state chirality of (M)-cis-(1) and (P)-trans-(2)-2-nitro-7-(dimethylamino)-9-(2',3'-dihydro-1'H-naphtho[2,1-b]-thiopyran-1'-ylidene)-9H-thioxanthene isdescribed. It is shown that while ground state chirality can be controlled photochemically by irradiation withlight of different wavelengths, the excited state chirality can be tuned either photochemically in a similarway or by appropriate choice of solvent. In benzene solution, circularly polarized luminescence of the twoisomers with opposite ground-state helicity, (M)-cis-1 and (P)-trans-2, revealed corresponding excited statesof opposite helicity. On the contrary, in n-hexane solution, circularly polarized luminescence was identicalfor the two forms indicating identical excited state chirality. Circularly polarized luminescence (CPL), steady-state and time-dependent fluorescence, and time-resolved microwave conductivity (TRMC) measurementsin both n-hexane and benzene are reported, which provide an explanation for the remarkable solventdependence of excited-state chirality.