Shi-xu Yi, J. Men, Difeng Wu
Jan 1, 2011
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Journal
Designed Monomers and Polymers
Abstract
A series of novel monomers of oligomers or polymers based on linear 1,4-phenylethynyl or 1,5-naphthylethynyl subunits, 1,4-bis(naphthalen-1-ylethynyl)benzene (8a) and its derivatives (8b–8i), has been synthesized and characterized. The UV absorption and fluorescence emission properties of these compounds were analyzed and discussed through the energy gap ( E ) between HOMO and LUMO orbitals, the orbital diagrams and the charge densities of related carbon atoms. It is evident from these results that the introduction of the electron-donating substituent (–OR) to the central phenylene ring of 8a and the introduction of electron-withdrawing substituent (–NO2) to the end of the conjugated system can efficiently improve its solubility, give rise to red-shift of maximum absorption and emission wavelength. But the introduction of electron-withdrawing substituent (–NO2) will lead dramatically decrease in fluorescence efficiency. The novel synthesized compounds 8b–8e have potential prospects as the monomers of oligomers or polymers based on linear 1,4-phenylethynyl or 1,5-naphthylethynyl subunits for their excellent solubility and optical properties.