1384954-15-7Relevant articles and documents
α,α′-Diarylacenaphtho[1,2-c]phosphole P-oxides: Divergent synthesis and application to cathode buffer layers in organic photovoltaics
Matano, Yoshihiro,Saito, Arihiro,Suzuki, Yuto,Miyajima, Tooru,Imahori, Hiroshi,Akiyama, Seiji,Otsubo, Saika,Nakamoto, Emi,Aramaki, Shinji
, p. 2305 - 2312,8 (2020/08/24)
A divergent method for the synthesis of α,α'- diarylacenaphtho[1,2-c]phosphole P-oxides has been established; α,α'-dibromoacenaphtho[c]phosphole P-oxide, which was prepared through a TiII-mediated cyclization of 1,8-bis(trimethylsilylethynyl) naphthalene, underwent a Stille coupling with three different kinds of aryltributylstannanes to afford the α,α'-diarylacenaphtho[c] phosphole P-oxides in moderate to good yields. X-ray crystallographic analyses and UV/Vis absorption/fluorescence measurements have revealed that the degree of π-conjugation, the packing motif, the electron-accepting ability, and the thermal stability of the acenaphtho[c]phosphole π-systems are finely tunable with the α-aryl substituents. All the P=O and P=S derivatives exhibited high stability in their electrochemically reduced state. To use this class of arene-fused phosphole π-systems as n-type semiconducting materials, we evaluated device performances of the bulk heterojunction organic photovoltaics (OPV) that consist of poly(3-hexylthiophene), an indene-C70 bisadduct, and a cathode buffer layer. The insertion of the diarylacenaphtho[c] phosphole P-oxides as the buffer layer was found to improve the power conversion efficiency of the polymer-based OPV devices. A convenient approach to α,α'-diarylacenaphtho[c]phosphole P-oxides through a Stille coupling of the α,α'-dibromo synthon has been developed. The effects of the α-aryl substituent on the structural, optical, and electrochemical properties have been revealed. The diarylacenaphtho[c]phosphole P-oxides were found to behave as promising cathode buffer materials in bulk heterojunction organic photovoltaics. Copyright
