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Syntheses and characterization of dithienyl-blocked hexapyrrin and its mononuclear complexes

Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. China

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Yating Fu

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Bin Zhu

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Glib Baryshnikov

Department of Science and Technology, Laboratory of Organic Electronics, Linköping University, Norrköping, SE-60174, Sweden

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Hao-Ling Sun

Department of Chemistry and Beijing Key Laboratory of Energy Conversion and Storage Materials, Beijing Normal University, Beijing 100875, P. R. China

E-mail Address: haolingsun@bnu.edu.cn

Corresponding author.

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Feng Sha

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Chengjie Li

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Xin-Yan Wu

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Hans Ågren

Department of Physics and Astronomy, Uppsala University, Box 516, SE-751 20 Uppsala, Sweden

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Qizhao Li

E-mail Address: zhaolq@ecust.edu.cn

Corresponding author.

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, and

Yongshu Xie

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https://doi.org/10.1142/S1088424623500335Cited by:0 (Source: Crossref)

Abstract

With the purpose to develop long chain-conjugated oligopyrrin-like compounds and their metal complexes, and thus achieve tunable near-infrared absorption, a dithienyl-blocked hexapyrrane $S_{2} - P_{6}$ was synthesized by acid-catalyzed [2+4+2] condensation, followed by oxidation with DDQ to afford dithiaoctapyrrin 1, and its mononuclear metal complexes 1-Cu and 1-Zn were synthesized by treating 1 with Cu(II) and Zn(II) acetates. All the compounds were systematically characterized by NMR/EPR, and HRMS. The crystal structures revealed that 1 adopts a double hook-like conformation. Whereas, both complexes 1-Cu and 1-Zn adopt spiral-hook hybrid conformations, showing smaller interplanar angles between the rings within the spiral part, compared with those in the hook-like counterpart of molecule 1, which is favorable for red-shifting the absorption. As expected, the absorption band edges for complexes 1-Cu and 1-Zn are red-shifted to ca. 1560 nm, compared with that of 1260 nm observed for 1.

Dedicated to Prof. Jonathan L. Sessler on the occasion of his 65th birthday

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