卟啉取代偶氮苯结构的合成、表征及光化学性质评估

Synthesis, Characterization and Evaluating Photochemical Properties of Porphyrin-substituted Azobenzene Structure.

作者信息

Erdemir Guler Yagiz, Topkaya Derya

机构信息

Department of Chemistry, Faculty of Science, Gazi University, Ankara, 06560, Turkey.

Department of Chemistry, Faculty of Science, Dokuz Eylul University, İzmir, 35160, Turkey.

出版信息

J Fluoresc. 2024 Jan;34(1):275-281. doi: 10.1007/s10895-023-03256-6. Epub 2023 May 19.

DOI:10.1007/s10895-023-03256-6

PMID:37204533

Abstract

Herein a new azobenzene-substituted porphyrin molecule was synthesized, characterized and its optoelectronic properties were investigated by combining the high optoelectronic properties of porphyrin with the photosensitive properties of azobenzene. The carboxylic acid of azobenzene was covalently connected to -OH group of the porphyrin ring by using Steglich esterification. Molecular structure of the obtained azobenzene-porphyrin (8), was elucidated, by FTIR, H and C NMR and HRMS. After structural characterization absorption and emission, characteristics were determined in solvents that have different. And also, optical and fluorescence behaviors in the range of different acid pH with trans-cis photoisomerization behaviors were investigated in aqueous-THF solution in acid media.

摘要

在此合成了一种新的偶氮苯取代卟啉分子，对其进行了表征，并通过将卟啉的高光电子性质与偶氮苯的光敏性质相结合来研究其光电性质。利用施陶丁格酯化反应将偶氮苯的羧酸与卟啉环的-OH基团共价连接。通过傅里叶变换红外光谱（FTIR）、氢核磁共振（¹H NMR）、碳核磁共振（¹³C NMR）和高分辨质谱（HRMS）对所得偶氮苯-卟啉（8）的分子结构进行了阐明。在结构表征之后，测定了其在不同溶剂中的吸收和发射特性。此外，还在酸性介质的水-四氢呋喃溶液中研究了其在不同酸性pH范围内的光学和荧光行为以及反式-顺式光异构化行为。