Abstract

Strong electron-donating functionality is desirable for many organic donor-π-bridge-acceptor (D-π-A) dyes. Strategies for increasing the electron-donating strength of common nitrogen-based donors include planarization of nitrogen substituents and the use of low resonance-stabilized energy aromatic ring-substituted nitrogen atoms. Organic donor motifs based on the planar nitrogen containing heterocycle indolizine are synthesized and incorporated into dye-sensitized solar cell (DSC) sensitizers. Resonance active substitutions at several positions on indolizine in conjugation with the D-π-A π-system are examined computationally and experimentally. The indolizine-based donors are observed to contribute electron density with strengths greater than triarylamines and diarylamines, as evidenced by UV/Vis, IR absorptions, and oxidation potential measurements. Fluorescence lifetime studies in solution and on TiO2 yield insights in understanding the performance of indolizine-based dyes in DSC devices. Indolizines are exceptionally strong organic donor building blocks for use in D-π-A dyes for dye sensitized solar cells. A series of indolizine-based dyes is synthesized for comparison to known common organic donor functionality. These dyes are studied computationally, electrochemically, spectroscopically, and in dye-sensitized solar cell devices.

Department(s)

Chemistry

Publication Status

Full Access

Comments

National Science Foundation, Grant 0955550

Keywords and Phrases

competing aromaticity; dye-sensitized solar cells; electron-rich building blocks; indolizine dyes; proaromatic structures

International Standard Serial Number (ISSN)

1614-6840; 1614-6832

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2024 Wiley; Wiley-VCH Verlag, All rights reserved.

Publication Date

01 Apr 2015

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Chemistry Commons

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