이온형 폴리아세틸렌인 폴리[N-(에틸술포네이트 소듐)-2-에티닐피리디늄의 합성과 특성연구 = Synthesis and Properties of an Ionic Polyacetylene: Poly[N-(ethylsulfonate sodium)-2-ethynylpyridinium bromide]

다국어 초록 (Multilingual Abstract)

A new ionic polyacetylene was prepared by the uncatalyzed polymerization of 2-ethynylpyridine using sodium 2-bromoethane sulfonate in high yield. The polymerization proceeded well in homogeneous manner to give a high yield of the polymer (yield: 78 %). The activated acetylenic triple bond of N-(ethylsulfonate sodium)-2-ethynylpyridinium bromide, formed at the first quaternarization process, was found to be susceptible to linear polymerization. The polymer structure was characterized by various instrumental methods to have the polyacetylene backbone structure with the designed substituent. The inherent viscosities of the resulting polymers were in the range of 0.12-0.15 dL/g and X-ray diffraction analysis data indicated that this polymer is mostly amorphous. The photoluminescence maximum peak was observed at 593 nm corresponding to a photon energy of 2.09 eV. The polymer exhibited the irreversible electrochemical behaviors in cyclic voltammetry result.

참고문헌 (Reference)

1 I. Yamaguchi, "Uncatalyzed synthesis of polyacetylene with viologen side groups and their chemical properties" 69 : 864-, 2009

2 K. M. Kim, "Synthesis of hybrid polyacetylene gels using octafunctional POSS iniatiator" 249 : 249-250, 2007

3 T. Masuda, "Synthesis of high polymers from substituted acetylenes: exploitation of molybdenum- and tungsten-based catalysts" 17 : 51-, 1984

4 제갈영순, "Synthesis and properties of poly(N-benzoyl-2-ethynylpyridinium chloride)" 한국공업화학회 17 (17): 282-286, 2011

5 Y. S. Gal, "Synthesis and properties of poly(2-ethynylpyridinium bromide) having propargyl side chains" 39 : 3151-, 2001

6 Hyun-Kuk Choi, "Synthesis and properties of an ionic polyacetylene with norbornene moieties" 한국공업화학회 16 (16): 214-219, 2010

7 Y. S. Gal, "Synthesis and properties of an ionic polyacetylene with aromatic heterocycles" 45 : 5679-, 2007

8 Y. Okamoto, "Synthesis and electronic properties of polypyridylacetylenes" 29 : 1311-, 1964

9 J. W. Park, "Synthesis and electrochemical properties of poly(1,6- heptadiyne) derivatives containing a carbazole moiety" 32 : 2789-, 1994

10 Yeong-Soon Gal, "Synthesis and electro-optical properties of self-doped ionic conjugated polymers: poly[2-ethynyl-N-(4-sulfobutyl)pyridinium betaine]" 한국물리학회 5 (5): 38-42, 2005

11 T. Masuda, "Substituted polyacetylenes" 45 : 165-, 2007

12 T. P. I. Saragi, "Spiro compounds for organic optoelectronics" 107 : 1011-, 2007

13 M. S. Freund, "Self-doped conducting polymers" WILEY 2007

14 C. I. Simionescu, "Polymerization of acetylene derivatives. Anion-radical salts of TCNQ with poly(vinyl- and ethynylpyridines)" 15 : 69-, 1978

15 Y. S. Gal, "Polymerization of 2-ethynylpyridine by transition metal chloride and organoaluminum compounds" 12 : 30-, 1988

16 P. Hany, "Polyanilines with covalently bonded alkylsulfonates as doping agent-synthesis and properties" 31 : 369-, 1989

17 S. K. Choi, "Poly(1,6-heptadiyne)-based materials by metathesis polymerization" 100 : 1645-, 2000

18 D. W. Kim, "Ordered multilayer nanocomposites prepared by electrostatic layer-by layer assembly between aluminosilicate nanoplates and substituted ionic polyacetylenes" 14 : 3925-, 2002

19 W. Lee, "Nanocrystalline CdS-water-soluble conjugated polymers: high performance photoelectrochemical cells" 90 : 263503-, 2007

20 G. K. Prasad, "Nanocomposite based on poly(Noctadecyl- 2-ethynylpyridinium bromide) and Mg0.04Nb1.66O5 nanosheets" 288 : 200-, 2005

21 W. Lee, "Manipulating interfaces in a hybrid solar cell by in situ photosensitizer polymerization and sequential hydrophilicity/hydrophobicity control for enhanced conversion efficiency" 92 : 193307-, 2008

22 G. Kwak, "Ionic polyacetylene with aromatic functional groups: synthesis and properties" 209 : 1769-, 2008

23 S. M. Lee, "Cyclodextrin-induced fluorescence enhancement of an ionic polyacetylene having phenylethynylpyridinium groups" 67 : 249-250, 2007

24 X. Song, "Conjugated polymers as efficient fluorescence quenchers and their applications for bioassays" 14 : 2342-, 2002

25 P. Zhou, "Conjugated phosphonium polyacetylenes" 38 : 595-, 1997

26 S. Subramanyam, "Conjugated ionic polyacetylenes. 4: polymerization of ethynylpyridines with bromine" 25 : 2065-, 1992

27 S. Subramanyam, "Conjugated ionic polyacetylenes, 2: a new polymerization method for substituted acetylenes" 12 : 23-, 1990

28 Y. Mao, "Composites of quaternized poly(pyridyl acetylene) and silver nanoparticles: nanocomposite preparation, conductivity and photoinduced patterning" 21 : 13627-, 2011

29 J. Liu, "Acetylenic polymers: syntheses, structures, and functions" 109 : 5977-, 2009

30 Yeong-Soon Gal*, "A Self-Doped Ionic Conjugated Polymer: Poly(2-ethynylpyridinium-Nbenzoylsulfonate) by the Activated Polymerization of 2-Ethynylpyridine with Ring-Opening of 2-Sulfobenzoic Acid Cyclic Anhydride" 대한화학회 25 (25): 777-778, 2004