Thiomethyl Derivatives of Two Oligo(p-phenylene vinylenes) as New Aggregation-Induced Piezofluorochromic Emitters

Xueqing Hou, Jing Ling, Navamoney Arulsamy, Jianqiang Huo

Department of Chemistry, University of Wyoming, Laramie, USA.
Key Laboratory of Eco-Environment Related Polymer Materials of Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, China.

DOI: 10.4236/msa.2013.46043                

Abstract

Two piezochromic fluorescent compounds are prepared by introducing thiomethyl substituents to the peripheralpositions of two related cyano oligo(p-phenylene vinylenes) (CN-OPV). The new derivatives, namely, 1,4-bis[2-cyano-2(4-thiomethylphenyl)ethenyl]benzene (TOPV1) and 1,4-bis(1-cyano-2-(4-thiomethylphenyl)ethenyl) benzene (TOPV2), are characterized by NMR, powder X-ray diffraction data (XRD) and differential scanning calorimetric (DSC) data. UV-Vis and fluorescence spectra are also measured. TOPV1 with the cyano groups farther away from the central aromatic ring is photoluminescent, and on application of pressure exhibits a more obvious color change and higher Stokes shift than those measured for TOPV2. We also observe piezochromic aggregation-induced emission (PAIE) for TOPV2, but TOPV1 does not exhibit any PAIE.

Keywords

Aggregation Induced Emission (AIE); Piezochromic Fluorophore; Excimer Fluorescence

Conflicts of Interest

The authors declare no conflicts of interest.

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