Synthesis, Characterization, and Cation-Induced Supramolecular Structures of Photochromic Bisthienylethene-Tetraazaporphyrin Hybrids (BTE-TAPs) Bearing Crown Ether Moieties

Lei Li; Xuan Sun

doi:10.1071/CH07440

RESEARCH ARTICLE

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Synthesis, Characterization, and Cation-Induced Supramolecular Structures of Photochromic Bisthienylethene-Tetraazaporphyrin Hybrids (BTE-TAPs) Bearing Crown Ether Moieties

Lei Li ^A and Xuan Sun ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Shandong University, Jinan 250100, China.

^B Corresponding author. Email: sunxuan@sdu.edu.cn

Australian Journal of Chemistry 61(8) 640-645 https://doi.org/10.1071/CH07440
Submitted: 21 December 2007 Accepted: 13 March 2008 Published: 15 August 2008

Abstract

A series of novel tetraazaporphyrinato (TAP) copper compounds 1–5 substituted with different numbers of 15-crown-5 voids and photochromic 1,2-bisthienylethenes (BTEs) were synthesized by ‘one-pot’ reaction and characterized by spectroscopic methods as well as elemental analysis. The effects of BTE and 15-crown-5 substituent number and molecular symmetry on the electronic absorption spectra, infrared spectra, photochromic performance and supramolecular structure formation induced by K⁺ ions have been systematically investigated. All the BTE-TAP hybrids presented photocyclization and cycloreversion with different quantum yields by irradiation with 365 and 700 nm light in CHCl₃ solution, respectively. The steric hindrance derived from the BTE substituents prevents the cofacial dimerization of the compounds, and only linear dimers formed as a result.

Acknowledgement

Financial support from the Natural Science Foundation of China, Chinese Academy of Sciences innovative projects, Ministry of Education of China, Natural Science Foundation of Shandong Province (Y2006B14), Department of Science and Technology of Shandong Province, and Shandong University is gratefully acknowledged.

References

Synthesis, Characterization, and Cation-Induced Supramolecular Structures of Photochromic Bisthienylethene-Tetraazaporphyrin Hybrids (BTE-TAPs) Bearing Crown Ether Moieties

Abstract

Acknowledgement

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