Impact of peripheral substituents in regioselective synthesis of position-10 or position-20 bromo-bacteriochlorins

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• 作者：Mykhaylo Dukh^a ; Penny Joshi^a ; Kei Ohkubo^b ; Walter Tabaczynski^c ; Nayan J. Patel^a ; ^d ; Joseph R. Missert^a ; Steve Zador^a ; Shunichi Fukuzumi^b ; ^e ; ^f ; ^{fukuzumi@chem.eng.osaka-u.ac.jp} ; Ravindra K. Pandey^a ; ^d ; ^{Ravindra.pandey@roswellpark.org}
• 关键词：Chlorin ; Bacteriochlorin ; Bovine serum albumin ; Density functional calculations
• 刊名：Tetrahedron Letters
• 出版年：2017
• 出版时间：1 March 2017
• 年：2017
• 卷：58
• 期：9
• 页码：851-854
• 全文大小：801 K
• 卷排序：58

文摘

A facile approach for the regioselective synthesis of 10-bromo and 20-bromo bacteriochlorins is discussed. Density functional calculations helped to determine the electron density at the peripheral positions of the tetrapyrrolic systems. A direct correlation between the electron density and regioselective bromination at the meso-position of the bacteriochlorin system was observed. Effect of solvent also showed a remarkable difference in electronic absorption spectra of the chlorin and bacteriochlorin system.