Issue 9, 2006
From the journal:

Journal of Materials Chemistry

Synthesis and characterization of new fluorescent two-photon absorption chromophores†

Ping-Hsin Huang,acd   Jiun-Yi Shen,a   Shin-Chien Pu,b   Yuh-Sheng Wen,a   Jiann T. Lin,*a   Pi-Tai Chou*b  and  Ming-Chang P. Yeh*c  

* Corresponding authors

a Institute of Chemistry, Academia Sinica, Taipei, Taiwan 115, Republic of China
E-mail: jtlin@chem.sinica.edu.tw
Fax: +886-2-27831237
Tel: +886-2-27898522

b Department of Chemistry, The National Taiwan University, Taipei, Taiwan 106, Republic of China

c Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 116, Republic of China

d Kang-Ning Junior College of Medical Care and Management, Taipei, Taiwan 114, Republic of China

Abstract

A series of dipolar and quadrupolar type two-photon absorption (TPA) compounds has been synthesized and TPA cross sections (σ) were measured by Ti∶sapphire femtosecond laser excitation fluorescence (λ = 800 nm). Among them, the compound [2,5-bis-[5-(4-diphenylaminophenylethynyl)thiophen-2-yl]-[1,3,4]oxadiazole], 12, has been structurally characterized by X-ray crystallography. The resulting data indicate that the structure of this compound possesses excellent coplanarity. The compounds have arylamines as the donor, and [1,3,4]oxadiazolyl, cyanovinyl or pyridazin-3,6-diyl moiety as the acceptor. Variation of arylamines and pendant alkyl groups was found to have a significant influence on σ values. By an appropriate combination of donor and acceptor, σ values of >103 GM (10−50 cm4s photon·molecule−1) can be achieved. One quadrupolar molecule (13) possessing an arylamine donor and a pyridazine acceptor has both a high σ value (1442 GM) and σ/MW (1.97 GM/g).

Graphical abstract: Synthesis and characterization of new fluorescent two-photon absorption chromophores

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Article information

DOI
https://doi.org/10.1039/B512524C
Article type
Paper
Submitted
05 Sep 2005
Accepted
10 Nov 2005
First published
05 Dec 2005

J. Mater. Chem., 2006,16, 850-857

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Synthesis and characterization of new fluorescent two-photon absorption chromophores

P. Huang, J. Shen, S. Pu, Y. Wen, J. T. Lin, P. Chou and M. P. Yeh, J. Mater. Chem., 2006, 16, 850 DOI: 10.1039/B512524C

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