Asymmetrically Substituted and 蟺-Conjugated 2,2鈥?Bipyridine Derivatives: Synthesis, Spectroscopy, Computation, and Crystallography

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• 作者：Ramakrishna Bodapati ; Monima Sarma ; Arunkumar Kanakati ; Samar K. Das
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：December 18, 2015
• 年：2015
• 卷：80
• 期：24
• 页码：12482-12491
• 全文大小：586K
• ISSN：1520-6904

文摘

A new series of monosubstituted styryl- and bistyryl-2,2鈥?bipyridine luminophores (compounds 16鈥?b>23) have been synthesized via Horner鈥揥adsworth鈥揈mmons reaction involving a monophosphonate and donor aromatic aldehydes. In the title chromophores, the amino donors are varied between acyclic and cyclic while the alkoxy donors are varied in terms of their number and position. The absorption maxima of these chromophores shift predominantly due to intramolecular charge transfer (ICT) between different donor and acceptor moieties. The title donor鈥揳cceptor molecules exhibit intense fluorescence in solution at room temperature, and their emissive behavior has been found to be highly sensitive to solvent polarity. The fluorescence spectra and quantum yields of all the chromophores were recorded in four different solvent media, and the chromophores 16, 17, 19, and 21 exhibit fluorescence in the solid state too. The influence of the nature and position of the donor functionalities in the conjugated backbone of the bipyridine moiety on the electronic absorption properties of the title chromophores (16鈥?b>23) has been demonstrated, which has further been corroborated by DFT and TD-DFT computation both in gas phase and in solution phase. The crystal structure of compound 18 has been described as a representative member of the family (16鈥?b>23).