Two-photon absorption chromophores with a tunable [2,2′]bithiophene core
Resource
Tetrahedron 62 (36): 8467-8473
Journal
Tetrahedron
Journal Volume
62
Journal Issue
36
Pages
8467-8473
Date Issued
2006
Author(s)
Chou, Chia-Feng
Huang, Tai-Hsiang
Lin, Jiann T.
Hsieh, Cheng-chih
Lai, Chin-Hung
Tsai, Chiitang
Abstract
Sonogashira coupling between 3,5,3′,5′-tetrabromo-[2,2′]bithiophene and various terminal alkynes provides two-photon absorption (TPA) chromophores 1-6, which possess electron donor (D) and/or acceptor (A) alkynyl substituents at 3(3′) and 5(5′) sites of the bithiophene core. The up-converted fluorescence emission excited at 800 nm (Ti:sapphire femtosecond laser, ∼100 fs pulses) was used to determine the two-photon absorption cross-sections (σ) of these compounds. The corresponding TPA cross-section (σ) values ranging from 132 to 1120 GM (10-50 cm4 s photon-1) can be fine-tuned by the substitutents. The quadrupolar-type (A-π-D-π-A) chromophore 5 exhibits the largest σ value (1120 GM) in CH2Cl2 upon 800 nm excitation. © 2006 Elsevier Ltd. All rights reserved.
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