Nonlinear optical and energy-level modulation of organic alkynes by click chemistry. Issue 27 (7th July 2016)

• Record Type: Journal Article
• Authors: Miao, Zongcheng; Han, Huihui; Wang, Dong; Gao, Hong; Gu, Jianming; Hu, Huiying
• Is Part Of: Tetrahedron. Volume 72:Issue 27/28(2016)
• Page Start: 4039
• Page End: 4046
• Publication Date: 2016-07-07
• Subjects: Nonlinear optical -- Energy-level modulation -- Click chemistry -- Near infrared absorption; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.05.035
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A series of novel donor–acceptor chromophores have been successfully synthesized in excellent yield by metal-free [2+2] click chemistry, which was effective in the energy-level modulation of organic the π-conjugation aniline derivatives. Meanwhile, structures of all products were fully characterized by NMR, IR, and MS. UV–vis spectra were enlarged with end-absorptions into the near infrared region in varying degrees by introducing TCNE, TCNQ, F4-TCNQ click reagents and correspondingly electrochemical tests revealed that the energy levels of HOMO and LUMO were effectively tuned. The third order nonlinear optical properties studied at 532/1064 nm with picosecond Z -scan techniques indicated that almost all products exhibited the high NLO properties, especially, for dyec 5, exhibiting third-order susceptibility χ (3) =1.83×10 −7 esu under laser beam at 1064 nm. Graphical abstract: