4,9- and 4,10-Substituted pyrenes: synthesis, successful isolation, and optoelectronic properties.
Org Biomol Chem
; 22(8): 1676-1685, 2024 Feb 21.
Article
em En
| MEDLINE
| ID: mdl-38299623
ABSTRACT
We report herein a way to prepare and purify optoelectronic functional 4,9- and 4,10-substituted pyrene isomers. By tuning the size of substituents, the designed 4,9- and 4,10-isomers can be successfully isolated by recycling preparative size-exclusion chromatography (SEC) and/or repeated recrystallization. The structure and purity of the isolated compounds 1-5 have been confirmed by 1H NMR, 13C NMR, and HRMS. The photophysical and electrochemical properties of compounds 1-5 have been studied in detail both experimentally and theoretically. The lowest transitions of these pyrenes, 1-5, are allowed, with moderate to high fluorescence quantum yields and radiative decay rates around 108 s-1. The differences between the electrochemical and photophysical properties of 4,9-, 4,10-, 1,6-, and 2,7-substituted isomers are compared and concluded.
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MEDLINE
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En
Ano de publicação:
2024
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Article