키랄성 곁가지를 가지는 나프탈렌 다이이미드
Naphthalene Diimides with N-substituted Chiral Groups
- 주제(키워드) 키랄성 , 나프탈렌 다이이미드 , 용해도
- 발행기관 아주대학교
- 지도교수 권오필
- 발행년도 2019
- 학위수여년월 2019. 2
- 학위명 석사
- 학과 및 전공 일반대학원 분자과학기술학과
- 실제URI http://www.dcollection.net/handler/ajou/000000028372
- 본문언어 영어
- 저작권 아주대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
Highly soluble materials are expected to play for solution process. However, many organic semiconducting materials both small molecule and polymer suffer from low solubility due to secondary bonds. In the past decades, introducing just long aliphatic chain has been used to increase the solubility but there had some drawbacks such as thermal stability and limitation of molecular design. In this study, we introduce the N-substituent chiral side-chains such as phenylethyl, indanyl, tetralinyl into naphthalene diimide (NDI) to increase solubility. The chiral side-chains include chiral-center carbon surrounding four different size and shape groups. Homochiral NDI with identical chiral side-chains has high solubility in dichlorobenzene compare to heterochiral NDI. In dichlorobenzene (DCB), homochiral NDI derivatives exhibit over 1 g/100g of solubility. On the other hand, heterochiral NDI derivatives have poor solubility below 0.4 g/100g in DCB. To investigate the origin, we confirm differential scanning calorimetry (DSC), crystal structure analysis, hirshfeld sulface analysis and free volume analysis. Homochiral NDI has no phase transition and high melting temperature compare to N,N'-Bis(1-hexyl)naphthalene-1,4,5,8-tetracarboxylic diimide (NDI-C6) with hexyl alkyl side-chain. Homchiral NDI exhibits asymmetric shape due to symmetric breaking side-chains. It has large free volume compare to heterochiral NDI. Therefore, introducing homochiral side-chains as solubilizing group are notable molecular design strategy for highly soluble materials.
more목차
Ι. Introduction 1
II. Experiments 4
II.1 Chemical Structures 4
II.2 Synthesis 6
II.2.1 Materials 6
II.2.2 Synthesis of Rylene Diimide Derivatives 7
II.3 General Characterization 8
II.3.1 Synthesis and 1H-NMR Analysis of Rylene Diimide Derivatives 8
III. Results and Discussion 19
III.1 UV-vis Absorption Spectra 19
III.2 Thermal Analysis 21
III.3 Highly Soluble Homochiral Materials 26
III.4 Crystal Structure of NDI Derivatives 29
III.4.1 Asymmetric Shaped Homochiral NDI 29
III.4.2 Molecular Orientation of NDI derivatives 33
IV. Conclusions 36
V. References 37
