한국섬유공학회지 (Textile Science and Engineering)

  • 제43권5호
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  • Pages.228-234
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  • 2006
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  • 1225-1089(pISSN)
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  • 2288-6419(eISSN)
한국섬유공학회 (The Korean Fiber Society)
권호 표지

$\pi$-공액화 고분자의 형광 감쇄를 이용한 형광 패터닝: 고분자 필름상에서와 전기방사된 플렉시블 섬유상 매트에서의 형광 패터닝

Fluorogenic Patterning Based on Fluorescence Quenching of $\pi$-Conjugated Polymers: Fluorescence Patterning on Films and on Flexible Electrospun Fibrous Mats

  • 김형준 (충남대학교 공과대학 바이오응용화학부 유기소재.섬유시스템전공(BK 21)) ;
  • 이정효 (충남대학교 공과대학 바이오응용화학부 유기소재.섬유시스템전공(BK 21)) ;
  • 곽찬규 (충남대학교 공과대학 바이오응용화학부 유기소재.섬유시스템전공(BK 21)) ;
  • 손원근 (충남대학교 공과대학 바이오응용화학부 유기소재.섬유시스템전공(BK 21)) ;
  • 박원호 (충남대학교 공과대학 바이오응용화학부 유기소재.섬유시스템전공(BK 21)) ;
  • 이택승 (충남대학교 공과대학 바이오응용화학부 유기소재.섬유시스템전공(BK 21))
  • Kim, Hyung-Jun (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering and BK 21, Chungnam National University) ;
  • Lee, Jung-Hyo (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering and BK 21, Chungnam National University) ;
  • Kwak, Chan-Kyu (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering and BK 21, Chungnam National University) ;
  • Son, Won-Keun (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering and BK 21, Chungnam National University) ;
  • Park, Won-Ho (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering and BK 21, Chungnam National University) ;
  • Lee, Taek-Seung (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering and BK 21, Chungnam National University)
  • 발행 : 2006.10.31
⟨ 이전 논문 다음 논문 ⟩

초록

Four copolymers of 9,9-dihexylfluorene and benzothiadiazole derivatives with or without quinoxaline were newly synthesized via Suzuki coupling reaction and characterized. The conjugated polymers with benzothiadiazole moiety in the main chain emitted green fluorescence, while their reduced polymers showed blue emission due to perturbation in the donor-acceptor structure. The polymers were spin-cast into thin films in the presence or absence of photoacid generator and well-defined fluorescence patterns were fabricated on the films by simple UV irradiation. The polymer was electrospun with poly(methyl methacrylate) to produce flexible fibrous mats. Fluorescence patterning was also conducted onto the electrospun fiber web to obtain a stable and flexible pattern without bending damage.

키워드

참고문헌

  1. T. A. Skotheim, R. L. Elsenbaumer, and J. Reynolds, Eds., 'Handbook of Conducting Polymers', 2nd Ed., Marcel Dekker, New York, 1997
  2. G. Hadziioannou and P. F. van Hutten, Eds., 'Semiconducting Polymers', Wiley-VCH, Weinheim, 2000
  3. P. Chandrasekhar, 'Conducting Polymers, Fundamentals and Applications', Kluwer Academic Publishers, Boston, 1999
  4. S. Miyata and H. S. Nalwa, Eds., 'Organic Electroluminescence Materials and Devices', Gordon and Breach, Amsterdam, 1997
  5. D. T. McQuade, A. E. Pullen, and T. M. Swager, 'Conjugated Polymer-based Chemical Sensors', Chem Rev, 2000, 100, 2537-2574 https://doi.org/10.1021/cr9801014
  6. M. Fukuda, K. Sawada, and K. Yoshino, 'Synthesis of Fusible and Soluble Conducting Polyfluorene Derivatives and Their Characteristics', J Polym Sci Part A: Polym Chem, 1993, 31, 2465-2471 https://doi.org/10.1002/pola.1993.080311006
  7. H. Kameshima, N. Nemoto, and J. Endo, 'Synthesis and Properties of Fluorene-based Fluorinated Polymers', J Polym Sci Part A: Polym Chem, 2001, 39, 3143-3150 https://doi.org/10.1002/pola.1296
  8. Q. Hou, Y. Xu, W. Yang, M. Yuan, J. Peng, and Y. Cao, 'Novel Red-emitting Fluorene-based Copolymers', J Mater Chem, 2002, 12, 2887-2892 https://doi.org/10.1039/b203862e
  9. M. T. Bernius, M. Inbasekaran, J. O'Brien, and W. Wu, 'Progress with Light-emitting Polymers', Adv Mater, 2000, 12, 1737-1750 https://doi.org/10.1002/1521-4095(200012)12:23<1737::AID-ADMA1737>3.0.CO;2-N
  10. B. A. D. Neto, A. S. Lopes, G. Ebeling, R. S. Goncalves, V. E. U. Costa, F. H. Quina, and J. Dupont, 'Photophysical and Electrochemical Properties of $\pi$-extended Molecular 2,1,3-Benzothiadiazole', Tetrahedron, 2005, 61, 10975-10982 https://doi.org/10.1016/j.tet.2005.08.093
  11. C. G. Bangcuyo, U. Evans, M. L. Myrick, and U. H. F. Bunz, 'Synthesis and Characterization of a 2,1,3-Benzothiadiazole-b-alkyne-b-1,4-bis(2-ethylhexyloxy)benzene Terpolymer, a Stable Low-band-gap Poly(heteroarylene-ethynylene)', Macromolecules, 2001, 34, 7592-7594 https://doi.org/10.1021/ma0112772
  12. Q. Fang, A. Tanimoto, and T. Yamamoto, 'Synthesis and Chemical Properties of New Photoluminescent Poly($\pi$-phenyleneethynylene) Containing an Electron-accepting Benzothiadiazole Unit and an Electron-donating Dialkoxybenzene Unit : Effect of Twisting of Main Chain on Photoluminescence', Synth Met, 2005, 150, 73-78 https://doi.org/10.1016/j.synthmet.2005.01.009
  13. T. Yamamoto, Z. Zhou, T. Kanbara, M. Shimura, K. Kizu, T. Maruyama, Y. Nakamura, T. Fukuda, B.-L. Lee, N. Ooba, S. Tomaru, T. Kurihara, T. Kaino, K. Kubota, and S. Sasaki, '$\pi$-Conjugated Donor-acceptor Copolymers Constituted of $\pi$-Excessive and $\pi$-Deficient Arylene Units. Optical and Electrochemical Properties in Relation to CT Structure of the Polymer', J Am Chem Soc, 1996, 118, 10389-10399 https://doi.org/10.1021/ja961550t
  14. B. C. Thompson, L. G. Madrigal, M. R. Pinto, T.-S. Kang, K. S. Schanze, and J. R. Reynolds, 'Donor-acceptor Copolymers for Red- and Near-infrared-emitting Polymer Light-emitting Diodes', J Polym Sci Part A: Polym Chem, 2005, 43, 1417-1431 https://doi.org/10.1002/pola.20578
  15. D. Li and Y. N. Xia, 'Electrospinning of Nanofibers : Reinventing the Wheel?', Adv Mater, 2004, 16, 1151-1170 https://doi.org/10.1002/adma.200400719
  16. G. Larsen, R. Velarde-Ortiz, K. Minchow, A. Barreto, and I. G. Loscertales, 'A Method for Making Inorganic and Hybrid (organic/inorganic) Fibers and Vesicle with Diameters in the Submicrometer and Micrometer Range via Sol-gel Chemistry and Electrically Forced Liquid Jets', J Am Chem Soc, 2003, 125, 1154-1155 https://doi.org/10.1021/ja028983i
  17. S. O. Han, W. K. Son, J. H. Youk, T S. Lee, and W. H. Park, 'Ultrafine Porous Fibers Electrospun from Cellulose Triacetate', Mater Lett, 2005, 59, 2998-3001 https://doi.org/10.1016/j.matlet.2005.05.003
  18. M. Bognitzki, H. Q. Hou, M. Ishaque, T. Frese, M. Hellwig, C. Schwarte, A. Schaper, J. H. Wendorff, and A. Greiner, 'Polymer, Metal, and Hybrid Nano- and Mesotubes by Coating Degradable Polymer Template Fibers (TUFT process)', Adv Mater, 2000, 12, 637-640 https://doi.org/10.1002/(SICI)1521-4095(200005)12:9<637::AID-ADMA637>3.0.CO;2-W
  19. R. A. Caruso, J. H. Schattka, and A. Greiner, 'Titanium Dioxide Tubes from Sol-gel Coating of Electrospun Polymer Fibers', Adv Mater, 2001, 13, 1577-1579 https://doi.org/10.1002/1521-4095(200110)13:20<1577::AID-ADMA1577>3.0.CO;2-S
  20. G. Han, B. Guo, L. Zhang, and B. Yang, 'Conductive Gold Films Assembled on Electrospun Poly(methyl methacrylate) Fibrous Mats', Adv Mater, 2006, 18, 1709-1716 https://doi.org/10.1002/adma.200600098
  21. J. K. Lee and T. S. Lee, 'Newly Synthesized Polybenzoxazole Derivative with an Adjacent Hydroxyphenyl Ring for Optical Sensing', J Polym Sci Part A: Polym Chem, 2005, 43, 1397-1403 https://doi.org/10.1002/pola.20612
  22. J. K. Lee, H.-J. Kim, T. H. Kim, C.-H Lee, W. H. Park, J. Kim, and T. S. Lee, 'A New Synthetic Approach for Polybenzoxazole and Light-induced Fluorescent Patterning on Its Film', Macromolecules, 2005, 38, 9427-9433 https://doi.org/10.1021/ma051112j
  23. B. A. DaSilveira Neto, A. S. Lopes, G. Ebeling, R. S. Goncalves, V. E. U. Costa, F. H. Quina, and I. Dupont, 'Reductive Sulfur Extrusion Reaction of 2,1,3-Benzothiadiazole Compounds: A New Methodology Using $NaBH_{4}$/ $CoCl_{2}6H_{2}O_{cat}$ as the Reducing System', Tetrahedron Lett, 2005, 46, 6843-6846 https://doi.org/10.1016/j.tetlet.2005.08.017
  24. D. Aldakov, M. A. Palacios, and P. Anzenbacher, Jr., 'Benzothiadiazoles and Dipyrrolyl Quinoxalines with Extended Conjugated Chromophores-f1uorophores and Anion Sensors', Chem Mater, 2005, 17, 5238-5241 https://doi.org/10.1021/cm050985p