Effect of Hyperconjugation on Photovoltaic Performance in Pseduo-2D Perylene Diimide Derivatives†
Zhilong He
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorYuwen Hong
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorGuangyu Li
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorTong Shan
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorYi Zhang
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorCorresponding Author
Hongliang Zhong
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Shenzhen Research Institute, Shanghai Jiao Tong University, Shenzhen, Guangdong, 518057 China
E-mail: [email protected]Search for more papers by this authorZhilong He
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorYuwen Hong
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorGuangyu Li
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorTong Shan
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorYi Zhang
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Search for more papers by this authorCorresponding Author
Hongliang Zhong
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai, 200230 China
Shenzhen Research Institute, Shanghai Jiao Tong University, Shenzhen, Guangdong, 518057 China
E-mail: [email protected]Search for more papers by this authorDedicated to the Special Issue of Emerging Investigators in 2023.
Comprehensive Summary
The π-π interaction is acknowledged as the predominant factor to determine the molecular packing in organic photovoltaic materials, while other non-covalent intermolecular interactions especially the σ-π hyperconjugation are often ignored. Herein, a perylene diimide (PDI) derivative named FIDT-PDI is designed and synthesized to shed light into the effect of hyperconjugation on the molecular packing and further the photovoltaic performance. Dynamic NMR and 2D NOE NMR demonstrate the formation of intermolecular σ-π hyperconjugation between the C—H bond of the PDI moiety in one molecule and the phenyl sidechain in another molecule of FIDT-PDI. Benefiting from the σ-π hyperconjugation, FIDT-PDI with twisted backbone reversely exhibits more ordered packing and stronger crystallinity compared with another PDI derivative FIDTT-PDI which has better planarity, consequently achieving superior PCE and higher carrier mobility. This contribution is the first paradigm to unravel the structure-property relationship between σ-π hyperconjugation of conjugated materials and corresponding photovoltaic performance.
Supporting Information
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Appendix S1: Supporting Information |
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