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Addressing the Trade-off in Long π-Bridge Dyes: Performance Optimization by Site-Specific Alkyl Chain Engineering.

Created on 23 Jun 2026

Authors

Haiping Li, Zongxue Wang, Xing Hu, Hancheng Zhu, Ji Zhang, Xinzhao Zhang

Published in

Journal of fluorescence. Jun 22, 2026. Epub Jun 22, 2026.

Abstract

Extending the π-conjugated bridge in donor-π-acceptor dyes improves light harvesting but systematically erodes interfacial charge-transfer performance. Here, density functional theory (DFT) and time-dependent DFT (TD-DFT) were used to investigate triphenylamine-cyanoacrylic acid dyes with one to four thiophene bridge units (T1-T4) alongside a site-specific alkyl-chain engineering strategy on the tetra-thiophene scaffold. Bridge extension progressively red-shifts the absorption maximum from 445 nm (T1) to 508 nm (T4) but simultaneously delocalizes excited-state electron density over the π-bridge, reducing effective electron density at the acceptor-TiO₂ interface and weakening adsorption stability, dye regeneration thermodynamics, and injection efficiency. Site-specific alkyl substitution addresses this conflict: the alternating a, d-substitution pattern constructs a bilateral steric fence that suppresses face-to-face π-π stacking and relocates dye-electrolyte interactions away from the conjugated core, thereby suppressing charge recombination. Lorentzian fitting of projected density-of-states profiles confirms that all alkylated variants retain ultrafast electron injection and near-unity injection efficiency, demonstrating that the steric modification is electronically decoupled from the injection channel. These results establish site-specific alkyl-chain engineering as an effective strategy for mitigating the trade-off inherent to long-bridge dye design.

PMID:
42332329
Bibliographic data and abstract were imported from PubMed on 23 Jun 2026.

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