Synthesis and Electronic Properties of Novel Donor–π–Acceptor-Type Functional Dyes with a Carbonyl-Bridged Bithiophene π-Spacer

Synthesis and Electronic Properties of Novel Donor–π–Acceptor-Type Functional Dyes with a Carbonyl-Bridged Bithiophene π-Spacer

In this study, we synthesized novel donor–π–acceptor (D–π–A) functional dyes bearing a carbonyl-bridged bithiophene as a π-conjugated spacer and evaluated the absorption and fluorescence properties as well as the photostability. The developed dyes <b>1-CO</b>–<b>3-CO</b> poss...

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Bibliographic Details
Main Authors: Miyu Ueda, Ryo Nagayama, Masaki Nagaoka, Naoya Suzuki, Shintaro Kodama, Takeshi Maeda, Shin-ichiro Kato, Shigeyuki Yagi
Format: Article
Language:English
Published: MDPI AG 2025-07-01
Series:Molecules
Subjects:
donor–π–acceptor-type dye
intramolecular charge transfer
panchromatic absorption
photostability
frontier orbital
Online Access:https://www.mdpi.com/1420-3049/30/15/3084
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Summary:In this study, we synthesized novel donor–π–acceptor (D–π–A) functional dyes bearing a carbonyl-bridged bithiophene as a π-conjugated spacer and evaluated the absorption and fluorescence properties as well as the photostability. The developed dyes <b>1-CO</b>–<b>3-CO</b> possess an <i>N</i>,<i>N</i>-diphenylaminophenyl electron donor unit and an electron acceptor unit such as a formyl group (<b>1-CO</b>), an (<i>N</i>,<i>N</i>-diethylthiobarbituryl)methylene moiety (<b>2-CO</b>), or a (3-dicyanomethylidene-1-indanon-2-yl)methylene moiety (<b>3-CO</b>). The absorption spectra of <b>1-CO</b>–<b>3-CO</b> in dichloromethane at room temperature showed absorption maxima at 569 nm, 631 nm, and 667 nm, respectively, and the stronger acceptors in <b>2-CO</b> and <b>3-CO</b> led to enhancement of the ICT character. In addition, <b>2-CO</b> and <b>3-CO</b> had a second absorption band in the visible region, showing panchromatic absorption properties. Electrochemical analyses of the developed dyes revealed that the carbonyl bridging group in the π-spacer contributes to stabilization of the frontier orbitals such as the highest occupied and lowest unoccupied molecular orbitals (HOMO and LUMO, respectively), in comparison with the referential dyes bearing a dibutylmethylene-bridged bithiophene spacer, <b>1-CBu<sub>2</sub></b>–<b>3-CBu<sub>2</sub></b>. The HOMO/LUMO stabilization brought about high photostability in the doped poly(methyl methacrylate) film.
ISSN:1420-3049

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