Synthesis and properties of NLO chromophores with fine-tuned gradient electronic structures

Xiaohua Ma, Fei Ma, Zhenhua Zhao, Naiheng Song*, Jianping Zhang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

55 Scopus citations


A novel series of heterocycle-based NLO chromophores based on different combinations of auxiliary donor (i.e., benzene, thiophene and pyrrole) and auxiliary acceptor (i.e., thiazole with different regiochemistries) were designed and synthesized. Due to the different electron-rich and poor nature of the auxiliary donors and acceptors, respectively, the resulting NLO chromophores have systematically varied ground-state electronic structures, as evidenced by the 1H NMR, CV and UV-vis investigations. The nonlinear optical properties of the resulting NLO chromophores were studied by UV-vis spectroscopy, Hyper-Rayleigh scattering (HRS), and semi-empirical computations. All the chromophores have very large molecular hyperpolarizabilities (β1000 nm) in the range of 704-1500 × 10-30 esu (or β0, 318-768 × 10-30 esu), which showed a great sensitivity to the gradient electronic structures. Upon increasing the electron density from benzene to thiophene and to pyrrole, substantial increases in β0 were observed; significantly larger β0 values were also observed for NLO chromophores based on "matched" thiazole (C2 is connected to the acceptor) than those based on "un-matched" thiazole (C5 is connected to the acceptor). TGA investigations showed good thermal stability for the resulting NLO chromophores. However, with the increase of electron density of the auxiliary donor, a decrease in thermal and photochemical stability was observed. It is interesting to note that NLO chromophores based on triarylamine as the donor and thiazole as the auxiliary acceptor exhibited not only high thermal stability but also very large β0 values.

Original languageEnglish (US)
Pages (from-to)2975-2985
Number of pages11
JournalJournal of Materials Chemistry
Issue number19
StatePublished - 2009

ASJC Scopus subject areas

  • General Chemistry
  • Materials Chemistry


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