Effect of Hyperconjugation on Photovoltaic Performance in Pseduo‐2D Perylene Diimide Derivatives

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) deriv...

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Bibliographic Details
Published in:Chinese journal of chemistry 2024-04, Vol.42 (7), p.725-730
Main Authors: He, Zhilong, Hong, Yuwen, Li, Guangyu, Shan, Tong, Zhang, Yi, Zhong, Hongliang
Format: Article
Language:English
Subjects:
Carrier mobility
Conformation
Diimide
Hydrogen bonds
Hyperconjugation
NMR
Nonfullerene acceptor
Nuclear magnetic resonance
Organic solar cells
Packing
Perylene diimide
Photovoltaics
Weak intermolecular interactions
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Summary: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. This work firstly unravels the effect of intermolecular σ‐π hyperconjugation on the molecular packing and further the optoelectronic properties.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202300616