Journal
CCS CHEMISTRY
Volume 3, Issue 6, Pages 1070-1080Publisher
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.021.202100956
Keywords
organic photovoltaics; nonfullerene acceptor; all-fused-ring design; C-H activation; stability
Categories
Funding
- National Key RAMP
- D Program of China [2019YFA0705900, 2017YFA0204701]
- National Natural Science Foundation of China [21661132006, 91833304]
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A new type of all-fused-ring electron acceptor (ITYM) has been designed and synthesized, showing extraordinary stability and promising performance compared to classical carbon-bridged INCN-type acceptors, opening up a new avenue for high-efficiency and -stability organic photovoltaics.
High-performance donor-acceptor electron acceptors containing 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (INCN)-type terminals are labile toward photooxidation and basic conditions, and new molecular designs toward electron acceptors that can achieve both high power conversion efficiencies and high stability are urgently needed. By replacing the central benzene ring in the classical ladder-type n-type semiconductor, 2,2'-(indeno[1,2-b]fluorene-6,12-diylidene)dimalononitrile, with the electron-rich 4,4,9,9-tetrahexyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene, we report herein the design of 2,2'-(7,7,15,15-tetrahexyl-7,15-dihydro-sindaceno[1,2-b:5,6-b']diindeno[1,2-d]thiophene-2,10 (2H)-diylidene)dimalononitrile (ITYM), a new type of all-fused-ring electron acceptor (AFRA). A threestep reaction including a key Pd-catalyzed double C-H activation/intramolecular cyclization is established for the efficient synthesis of such type of electron acceptors. ITYM is confirmed by singlecrystal X-ray analysis, which shows a planar nonacyclic structure with strong pi-pi stacking. Compared with the classical carbon-bridged INCN-type acceptors, ITYM exhibits extraordinary stability with very promising performance. The AFRA concept opens a new avenue toward high-efficiency and -stability organic photovoltaics (OPVs).
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