尾-Functionalized Push鈥揚ull opp-Dibenzoporphyrins

详细信息    查看全文

• 作者：R. G. Waruna Jinadasa ; Yuanyuan Fang ; Siddhartha Kumar ; Allen J. Osinski ; Xiaoqin Jiang ; Christopher J. Ziegler ; Karl M. Kadish ; Hong Wang
• 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：12076-12087
• 全文大小：748K
• ISSN：1520-6904

文摘

The synthesis of a series of 尾-functionalized push鈥損ull dibenzoporphyrins was realized. These porphyrins display subtle push鈥損ull effects, demonstrating the exceptional tunability of their electronic and electrochemical properties. The UV鈥搗is spectra of these porphyrins show unique absorption patterns with shouldered Soret bands and extra absorptions in the Q-band region. Stronger electron-withdrawing groups display more significant bathochromic shifts of the Soret bands. The fluorescence spectra of these porphyrins show strong near-IR emission bands (600鈥?50 nm). In particular, fluorescence quenching effect was observed for pyridyl carrying push鈥損ull porphyrin 4c in the presence of an acid. TFA titration study of 4c using UV鈥搗is and fluorescence spectroscopy reveals that the fluorescence quenching can be mainly attributed to the protonation of the pyridyl groups of 4c. The versatile synthetic methods developed in this work may open a door to access a large number of functionalized organic materials that are currently unavailable. The structure鈥損roperty studies provided in this work may provide useful guidelines for the design of new generations of materials in dye-sensitized solar cells, in nonlinear optical applications, as fluorescence probes, as well as sensitizers for photodynamic therapy.