Efficient Synthesis of Block Copolymers Bearing Donor-Acceptor Chromophores for Second-Order Nonlinear Optical Applications

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  • Li Yongrong
    Department of Organic and Polymeric Materials, Tokyo Institute of Technology
  • Tsuboi Yong-Kazumi
    Department of Organic and Polymeric Materials, Tokyo Institute of Technology
  • Michinobu Tsuyoshi
    Global Edge Institute, Tokyo Institute of Technology PRESTO, Japan Science and Technology Agency (JST)
  • Ishida Yoshihito
    Department of Organic and Polymeric Materials, Tokyo Institute of Technology
  • Hirai Tomoyasu
    Department of Organic and Polymeric Materials, Tokyo Institute of Technology
  • Hayakawa Teruaki
    Department of Organic and Polymeric Materials, Tokyo Institute of Technology
  • Kakimoto Masa-aki
    Department of Organic and Polymeric Materials, Tokyo Institute of Technology

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Block copolymers composed of unsubstituted polystyrene and electron-rich alkyne functionalized polystyrene segments were prepared by atom transfer radical polymerization (ATRP) of N,N-didodecyl-4-[(4-vinylphenyl)ethynyl]aniline (2) with bromine-terminated polystyrene (1). Subsequently, the atom-economic addition reaction between electron-rich alkynes and tetracyanoethylene (TCNE) was applied as an efficient post-functionalization method to introduce donor-acceptor chromophores. All polymers were comprehensively characterized by GPC, 1H NMR, IR and UV-Vis spectroscopies, and electrochemistry. The TCNE-adducted polymers showed intense charge-transfer (CT) bands, well-defined redox activities, and good thermal stability. Furthermore, the second harmonic generation (SHG) of the spin-coated polymer thin films on a glass slide was measured before and after electric poling, and the SHG coefficient (d33) of the poled thin film reached 3.0 pm V-1.

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