Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 50, Pages 11680-11687Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201902080
Keywords
cyclic voltammetry; fluorescence; oxidative coupling; porphycenes; porphyrinoids
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Funding
- JSPS KAKENHI [JP17H04875, JP17H05161, JP16H04119, JP18H04265]
- Shitagau Noguchi Foundation
- Mazda Foundation
- Nissan Chemical Corporation
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The main obstacle to the widespread application of porphycenes lies in the lack of efficient and economical methods for their production. Discovery of new synthetic methodologies for porphycene derivatives are important for fine-tuning of their optical and electrochemical properties. Herein, the preparation of a set of AABB-, ABAB-, and ABBA-type meso-tetrasubstituted unsymmetric porphycenes is reported. Their synthesis involved the acid-catalyzed oxidative coupling of AA-and BB-dipyrroethenes, or AB-type dipyrroethenes, as precursors in yields of up to 19%. The structures were unambiguously confirmed by X-ray crystallography. The type and position of substituents in the unsymmetric porphycenes enabled fine-tuning of the optical and electronic properties, which are discussed in terms of their UV/Vis absorption, fluorescence spectroscopies, cyclic voltammetry, and density functional theory calculations.
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