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Fine-tuning the molecular energy levels by incorporating thiophene units onto the π-backbone of core-expanded naphthalene diimides
引用本文:Dong Lu,Xiao-Chun Yang,Bing Leng,Xiao-Di Yang,Cong-Wu Ge,Xue-Shun Jia,Xi-Ke Gao. Fine-tuning the molecular energy levels by incorporating thiophene units onto the π-backbone of core-expanded naphthalene diimides[J]. 中国化学快报, 2016, 27(7): 1022-1026. DOI: 10.1016/j.cclet.2016.05.003
作者姓名:Dong Lu  Xiao-Chun Yang  Bing Leng  Xiao-Di Yang  Cong-Wu Ge  Xue-Shun Jia  Xi-Ke Gao
作者单位:a Department of Chemistry, College of Science, Shanghai University, Shanghai, 200444, China;b Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China;c Laboratory of Advanced Materials, Fudan University, Shanghai, 200433, China
基金项目:This study was supported financially by the National Natural Science Foundation of China (Nos. 21302212 and 21522209) and the “Strategic Priority Research Program” (No. XDB12010100).
摘    要:


Fine-tuning the molecular energy levels by incorporating thiophene units onto the π-backbone of core-expanded naphthalene diimides
Dong Lu,Xiao-Chun Yang,Bing Leng,Xiao-Di Yang,Cong-Wu Ge,Xue-Shun Jia,Xi-Ke Gao. Fine-tuning the molecular energy levels by incorporating thiophene units onto the π-backbone of core-expanded naphthalene diimides[J]. Chinese Chemical Letters, 2016, 27(7): 1022-1026. DOI: 10.1016/j.cclet.2016.05.003
Authors:Dong Lu  Xiao-Chun Yang  Bing Leng  Xiao-Di Yang  Cong-Wu Ge  Xue-Shun Jia  Xi-Ke Gao
Affiliation:a Department of Chemistry, College of Science, Shanghai University, Shanghai, 200444, China;b Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China;c Laboratory of Advanced Materials, Fudan University, Shanghai, 200433, China
Abstract:A series of core-expanded naphthalene diimides (NDI-DTYM) and thiophene-based derivatives (1a-c) were designed and synthesized to investigate the relationship between molecular structures and the highest occupied molecular orbital (HOMO) energy levels but has little impact on the lowest unoccupied molecular orbital (LUMO) energy levels. The results demonstrated that increasing the number of thiophene units can gradually elevate the HOMO energy levels but had little impact on the LUMO energy levels. The n-channel organic field-effect transistors (OFETs) based on 1b and 1c have demonstrated that these almost unchanged LUMO energy levels are proper to transport electrons.
Keywords:Naphthalene diimide  Thiophene  Molecular energy level  Organic transistor  Organic semiconductor  
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