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Theoretical insight into linear optical and two-photon absorption properties for a series of N-arylpyrrole-based dyes.

Authors
Type
Published Article
Journal
Organic & Biomolecular Chemistry
1477-0539
Publisher
The Royal Society of Chemistry
Publication Date
Volume
10
Issue
37
Pages
7527–7535
Identifiers
DOI: 10.1039/c2ob25916h
PMID: 22890854
Source
Medline
License
Unknown

Abstract

N-arylpyrrole-based dyes possessing excellent opto-electronic properties are promising candidates for two-photon fluorescence labeling materials. The systematic investigation of novel N-arylpyrrole derivatives is of great importance for both fine-tuning electronic spectra and designing two-photon absorption (2PA) materials. We thoroughly studied influences of the π-conjugated center and N-substituted pyrrole moieties on the linear optical and 2PA properties. Our results show that introducing N-arylpyrrole produces bathochromic-shifts of the absorption and emission bands and an enhancement of the 2PA cross section (δ(max)), demonstrating that the electron-rich pyrrole moieties can efficiently increase intramolecular charge transfer. Substitution of fluorenyl with benzothiadiazole produces the lower energy gap, higher emission lifetime, red-shift of 2PA spectra and larger δ(max). The absorption and emission bands are highly dependent on the nature of the active building blocks. The aromatic rings attached to pyrrole can modulate the absorption peaks in the high energy and thus subtly modify the electronic properties.

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