Synthesis and Properties of Phenanthrene-Containing Expanded Porphyrin-Based BODIPY Derivatives

Two phenanthrene-containing expanded porphyrins were synthesized by acid-catalyzed condensation and subsequently complexed with boron trifluoride etherate to afford BODIPY derivatives. Their structures and properties were investigated by spectroscopic, crystallographic, and computational methods. Changing the meso-substituent from 3,5-di-tert-butylphenyl (1) to 2,4,6-trimethylphenyl (2) significantly affects their photophysical properties. Notably, 2 exhibits large Stokes shifts (3471-3739 cm-1) and moderate fluorescence quantum yields (31-44%) in different organic solvents.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-14
DOI
https://doi.org/10.1021/acs.joc.6c01131
Primary Topic
Porphyrin and Phthalocyanine Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis and Properties of Phenanthrene-Containing Expanded Porphyrin-Based BODIPY Derivatives

Cun Bo Yang, Shuo Wang, Zongqi Zhang, Hao Chen et al.
The Journal of Organic Chemistry
Porphyrin and Phthalocyanine Chemistry
article

Synthesis and Properties of Phenanthrene-Containing Expanded Porphyrin-Based BODIPY Derivatives

Cun Bo Yang, Shuo Wang, Zongqi Zhang, Hao Chen, Jingna Li, Yaowen Liu, Haiyu Ma, Dasheng Geng, Wenjie Lu, Baichuan Liu
article en

Abstract

Two phenanthrene-containing expanded porphyrins were synthesized by acid-catalyzed condensation and subsequently complexed with boron trifluoride etherate to afford BODIPY derivatives. Their structures and properties were investigated by spectroscopic, crystallographic, and computational methods. Changing the meso-substituent from 3,5-di-tert-butylphenyl (1) to 2,4,6-trimethylphenyl (2) significantly affects their photophysical properties. Notably, 2 exhibits large Stokes shifts (3471-3739 cm-1) and moderate fluorescence quantum yields (31-44%) in different organic solvents.

The Journal of Organic Chemistry
Shanghai University (CN), Suzhou University of Technology (CN)
Natural Science Research of Jiangsu Higher Education Institutions of China
Openalex Percentile: Top 28%
Porphyrin and Phthalocyanine Chemistry
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