올레핀 복분해를 통한 ProDOT 유도체의 합성 = Synthesis of ProDOT derivatives via olefin metathesis

다국어 초록 (Multilingual Abstract)

The purpose of this study is develop new synthetic methodology to synthesize the monomers for conducting polymers having various functional groups. The procedures known for monomers mainly rely on individual synthetic route for each monomer. The idea of the study lies on that the intermediate is first synthesized and then a variety of monomers can be efficiently derived from the intermediate via a simple synthetic method. In this study, both MProDOT and PRoDOT-allyl was synthesized as the intermediates. Olefin cross-metathesis of MProDOT and various terminal alkenes afforded MProDOT derivatives equipped with various functional groups and the subsequent hydrogenation upon them gave various alkyl substituted ProDOT derivatives. In addition, olefin cross-metathesis of ProDOT-allyl and terminal alkenes also yielded various alkyl substituted ProDOT-allyl derivatives. The procedure was also extended over the alkenes with functional groups such as halides, nitrile, and others. In conclusion, olefin cross-metathesis of MProDOT and ProDOT-allyl with various alkenes provided an efficient route for ProDOT derived monomers in moderate to good yields.

목차 (Table of Contents)

• 제 1 장 서 론 1
• 1.1. 전도성 고분자 1
• 1.1.1. 전도성 고분자의 역사 1
• 1.1.2. 전자적 구조 4
• 1.1.3. 전기적 특성 8
• 1.1.4. 응용 분야 11
• 1.2. 올레핀 복분해 12
• 1.2.1. 올레핀 복분해 반응 12
• 1.2.2. 복분해 반응의 응용 13
• 제 2 장 연구의 배경 및 동향 14
• 제 3 장 연구 목적 17
• 제 4 장 실험 내용 20
• 4.1. 시료 및 기기 20
• 4.2. 합성방법 21
• 4.2.1. MProDOT-octene 21
• 4.2.2. MProDOT-decene 21
• 4.2.3. 2,2-Thiodiacetic diethyl ester 21
• 4.2.4. Diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate 22
• 4.2.5. diethyl 2-allylmalonate 22
• 4.2.6. 2-allylpropane-1,3-diol 23
• 4.2.7. diethyl 3-allyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylate 23
• 4.2.8. 3-allyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylic acid 24
• 4.2.9. ProDOT-allyl 24
• 4.2.10. ProDOT-allyl-octene 25
• 4.2.11. ProDOT-allyl-decene 25
• 4.2.12. ProDOT-allyl-allylbromide 26
• 4.2.13. DiProDOT-allyl 26
• 제 5 장 결과 및 토의 27
• 5.1. MProDOT 27
• 5.1.1. MProDOT 합성 27
• 5.1.2. MProDOT의 교차복분해 28
• 5.2. ProDOT-allyl 29
• 5.2.1. ProDOT-allyl 합성 29
• 5.2.2. ProDOT-allyl의 교차복분해 31
• 제 6 장 결 론 34
• 참 고 문 헌 35
• 부 록 37