Facile synthesis of functional poly(vinylene sulfide)s containing donor–acceptor chromophores by a double click reaction

Abstract

aThe new electronically active poly(vinylene sulfide)s containing the dialkylaniline-substituted electron-rich alkynes in the side chains were designed and synthesized by the 'thiol-click' polymerization. Subsequently, the donor-acceptor chromophores were introduced into the side chains of the polymer by the [2+2] click reaction as an efficient postfunctionalization method. The polymers showed good solubility in common organic solvents and the high thermal stability. The photophysical and electrochemical properties, as well as the click reactions, were characterized by means of UV-vis absorption spectroscopy, cyclic voltammetry, ect. After the introduction of donor-acceptor chromophores, the polymer showed a strong charge-transfer (CT) band in the visible absorption region, potent redox activities and a narrow band gap compared with the precursors. In addition, the third-order nonlinear properties, including the nonlinear absorption and the nonlinear susceptibilities, were investigated by using Z-scan techniques. A typical saturable absorption behavior was observed for the third order nonlinear absorption, with the nonlinear absorption coefficients (β) values of the polymer being -9.0×10 -12 m/W. Please do not adjust marginsPlease do not adjust margins click'), and the whole conjugated structures for main chains were designed. We hope better NLO properties because of the longer conjugated structures, but the similar results were obtained here. It was suggested that the moieties from [2+2] click reagents affected greater than those of conjugated structures.

Asymmetric side-chain engineering in semiconducting polymers: a platform for greener processing and post-functionalization of organic electronics

“…5 Another important feature of SPs is the potential for postfunctionalization through careful selection and incorporation of chemical motifs, allowing for the development of multifunctional organic electronics. 6,7 It is therefore unsurprising that these materials have been explored for applications in many emerging technologies, including skin-like electronics, large area flexible and plastic photovoltaics, conformable solid-state batteries, and high-precision biological and chemical sensors. [8][9][10][11][12][13] While these attributes are highly sought after, the mass production and commercialization of organic electronics is currently restrained by two major factors.…”

Post-polymerisation approaches for the rapid modification of conjugated polymer properties

“…For example, alkyne containing poly(vinylene sulfide) was reacted with TCNE, resulting in the formation of donor-acceptor chromophores (P12) with strong intramolecular charge-transfer interactions. 76 Overall, the CA-RE approach clearly results in significant changes to the optical and electronic properties of the polymers. However, the requirement for very electron-rich starting alkynes and the limited degree of functionalisation in some cases are drawbacks.…”

“…For example, alkyne containing poly(vinylene sulfide) was reacted with TCNE, resulting in the formation of donor–acceptor chromophores (P12) with strong intramolecular charge-transfer interactions. 76 …”

Optical Properties of New Third-Order Nonlinear Materials Modified by Click Chemistry

“…Currently, organic materials are being widely studied for their third-order nonlinear optical (NLO) properties thanks to the great nonlinear figure, high damage verge, super quick response time, and ability to modify material properties (molecular engineering) [ 1 , 2 ]. For photonic applications, resources with enormous third-order ocular nonlinearities, as well as debauched nonlinear optical properties, are found to be very important.…”