• An Ionic Polyacetylene Derivative from the Quaternization Polymerization of 2-Ethynylpyridine using 2-(Bromomethyl)naphthalene

  • Taehyoung Kim, Sung-Ho Jin*, Jongwook Park**, and Yeong-Soon Gal***,†

  • Advanced Functional Polymers Research Center, Korea Research Institute of Chemical Technology, Daejeon 34114, Korea
    *Department of Chemistry Education, Pusan National University, Busan 46279, Korea **Department of Chemical Engineering, Kyunghee University, Suwon 17104, Korea ***Department of Fire Safety, Kyungil University, Gyeongsan 38428, Korea

  • 2-(브로모메틸)나프탈렌에 의한 2-에티닐피리딘의 4차염화 중합을 통한 이온성 폴리아세틸렌 유도체

  • 김태형 · 진성호* · 박종욱** · 제갈영순***,†

  • 한국화학연구원 고기능고분자연구센터, *부산대학교 화학교육과, **경희대학교 화학공학과, ***경일대학교 소방방재학과

  • Reproduction, stored in a retrieval system, or transmitted in any form of any part of this publication is permitted only by written permission from the Polymer Society of Korea.

Abstract

In this manuscript, we introduced a new ionic polyacetylene derivative via in-situ quaternization polymerization of 2-ethynylpyridine using 2-(bromomethyl)naphthalene without any additional initiator or catalyst. The monomeric N-substituted-2-ethynylpyridinium salts firstly formed from the quaternization reaction of 2-ethynylpyridine and 2-(bromomethyl)naphthalene was found to yield the corresponding ionic polyacetylene in high yields via the self-initiated polymerization. The chemical structure of the polymer was characterized by such instrumental methods as infrared spectroscopy (IR), nuclear magnetic resonance (NMR) spectroscopies, UV-visible spectroscopies to have the polyacetylene backbone structure with the designed substituets. The inherent viscosities of the resulting polymers were in the range of 0.10-0.19 dL/g and X-ray diffraction analysis data indicated that this polymer is mostly amorphous. The synthesized polymer exhibited a maximum absorption peak at 448 nm, and the photoluminescence emission peak was observed at 509 nm with green emission, corresponding to a photon energy of 2.44 eV. Cyclic voltammetry (CV) measurements of the synthesized polymer demonstrated reproducible and stable electrochemical behavior over the potential range from −1.85 V to 1.55 V (vs. Ag/AgNO3), showing two irreversible redox peaks at both the oxidation and reduction potentials.


별도의 개시제나 촉매의 도움 없이 2-(브로모메틸)나프탈렌을 사용한 2-에티닐피리딘의 4차염화 중합을 통하여 새로운 이온성 폴리아세틸렌 유도체를 합성하였다. 첫 반응단계인 2-(브로모메틸)나프탈렌에 의한 2-에티닐피리딘의 4차염화 반응으로 생성된 단량체 종인 N-치환-2-에티닐피리디늄 염의 활성화된 아세틸렌 삼중 결합의 중합반응으로 폴리{2-에티닐-N-[(2-메틸렌)나프탈렌]피리디늄 브로마이드}(PEMNPB)를 높은 수율로 합성하였다. Infrared spectroscopy(IR), nuclear magnetic resonance(NMR), UV-visible 스펙트럼 분석을 통해 합성한 고분자의 분자구조를 확인하였으며 그 결과 폴리아세틸렌 골격에 N-[(2-메틸렌)나프탈렌]피리디늄 브로마이드 치환기가 도입된 이온성 공액구조 고분자임을 알 수 있었다. 합성한 고분자의 고유 점도는 0.10-0.19 dL/g 범위였으며 X-선 회절 분석 결과 이 고분자는 대부분 비정질 상이었다. 이 고분자의 흡수 장파장 최대 피크는 448 nm이었고, 광발광 피크는 509 nm에서 녹색으로 관찰되었는데, 이는 2.44 eV의 광자 에너지에 해당하는 것이다. 합성 고분자에 대한 순환 전압 전류법(CV) 측정 결과, -1.85 V에서 1.55 V(vs. Ag/AgNO3) 범위에서 재현성과 안정성이 있는 전기화학적 거동을 보였으며 산화 및 환원 전압에서 각각 두 개의 비가역적 산화환원 피크를 나타내었다.


Keywords: polyacetylene, 2-ethynylpyridine, 2-(bromomethyl)naphthalene, quaternization polymerization, cyclic voltammogram.

  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2025 Impact Factor : 1.0
  • Indexed in SCIE

This Article

  • 2026; 50(5): 762-769

    Published online Sep 25, 2026

  • 10.7317/pk.2026.50.5.762
  • Received on Jun 5, 2026
  • Revised on Jul 27, 2026
  • Accepted on Jul 29, 2026

Correspondence to

  • Yeong-Soon Gal

  • Department of Fire Safety, Kyungil University, Gyeongsan 38428, Korea

  • E-mail: ysgal@kiu.kr