여러가지 전자주개-전자받개(C60) 다이오드의 합성과 특성 = Synthesis and Characterization of Various Electron-donor-acceptor(C60) Dyads

다국어 초록 (Multilingual Abstract)

There has been a growing interest to synthesize various electron-donor and electron-acceptor systems in which intramolecular charge transfer interactions eventually produce an efficient and long-lived photo-induced charge separation. In these systems the through bond interaction via the bridge mainly depends on the nature of the bridge such as conjugation, rigidity and distance, as well as the strength of the donor- and acceptor moieties. In addition, spatial array of donor and acceptor moieties gives more influential effects to these systems.
In line with these aspects, seven novel donor-acceptor(C60) dyads 1-7, which have different numbers and kinds of donors, respectively, have been synthesized and characterized by spectroscopic methods such as 1H-NMR, 13C-NMR, FT-IR and MALDI-TOF mass. Electrochemical properties from cyclic voltammetry and photophysical properties from absorption and emission spectroscopies were discussed.

국문 초록 (Abstract)

분자 내 전하전달현상 (intramolecular charge-transfer interaction) 을 나타내는 전자주개(electron-donor)-전자받개(electron acceptor) 구조를 가진 화합물들에 대한 연구가 활발히 진행되고 있는 가운데, 전자받개 성분으로서 플러렌(C60)과 전자주개 성분으로서 디메틸(혹은 페닐)아닐린, 페로센, 트리페닐아민 등의 구조를 함께 가진 화합물 1-7 을 합성하였다. 이와 같이 합성된 전자주개의 화학종, 전자받개와의 거리, 전자주개로서 도입된 기능기의 수 등이 다른 화합물들은 각각 1H-NMR, 13C-NMR, FT-IR, MALDI-TOF mass 분광법을 통해 그들의 성공적인 합성 및 구조와 성질을 규명하였다. 나아가, UV/Vis, fluorescence 그리고 순환전류법(cyclic voltammetry) 실험으로 전자전달 현상을 관찰하고 전기화학적 성질을 측정하였다.

목차 (Table of Contents)

• I. Introduction 1
• II. Results and Discussion
• 1. Bis-aniline substituted methanofullerenes 1 and 2 5
• 2. Bis-aniline substituted ethenylmethanofullerenes 3 and 4 10
• 3. [Two vinylferrocenes]-triphenylamine-C60 dyad 5 11
• 4. Triphenylamine-C60 dyads 6 and 7 18
• III. Experimentals
• 1. Synthesis of bis-aniline substituted [6,6]methanofullerenes 1 and 2 19
• 1) Bis(N,N’-dimethylaniline)[6,6]methanofullerene (1) 19
• 2) Bis(N,N’-diphenylaniline)[6,6]methanofullerene (2) 20
• 2. Synthesis of bis-aniline substituted vinylene-[6,6]methano-fullerenes 3 and 4 22
• 1) Bis(N,N’-dimethylaniline)-ethenyl[6,6]methanofullerene (3) 22
• 2) Bis(N,N’-diphenylaniline)-ethenyl[6,6]methanofullerene (4) 22
• 3. Synthesis of [Two vinylferrocenes]-triphenylamine-C60 dyad 5 24
• 1) 4’,4’’-Divinylferrocenyltriphenylamine [6,6]methanofullerene (5) 24
• 4. Synthesis of triphenylamine-C60 dyads 6 and 7 26
• 1) 4’-Methoxytripenylamine 4-fulleropyrrolidine (6) 26
• 2) 4’,4’’-Dimethoxytripenylamine 4-fulleropyrrolidine (7) 28
• IV. References 31
• V. Spectrum 33