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Towards the synthesis of poly(azafulleroid)s: main chain fullerene oligomers for organic photovoltaic devices
Author(s) -
Bregadiolli Bruna A,
Ramanitra Hasina H,
Ferreira Rodrigo Marques,
Corcoles Laura,
Gomes Milton S,
Kang Lauren,
Combe Craig MS,
Silva Hugo Santos,
Lavarda Francisco C,
Bégué Didier,
DagronLartigau Christine,
Rocco Maria Luiza M,
Luscombe Christine K,
Olivati Clarissa A,
Graeff Carlos FO,
Hiorns Roger C
Publication year - 2017
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.5419
Subject(s) - comonomer , fullerene , molecular orbital , steric effects , polymer , polymer chemistry , materials science , molecule , chemistry , organic solar cell , computational chemistry , chemical engineering , organic chemistry , copolymer , engineering
For the first time, imino chemistry is explored for the synthesis of main chain fullerene oligomers and low‐molecular‐weight polymers. Oligo(aziridinofullerene)s and low‐molecular‐weight poly(aziridinofullerene)s (PAFs) are prepared by 1,3‐dipolar cycloadditions of bis(azidoalkyl) comonomers to C 60 . The effect of the steric bulk of the comonomer is studied and it is found that PAF solubilities and molecular weights are increased with longer comonomer side‐chains. Initial and promising photovoltaic characterizations show commensurate improvements in properties. Interestingly, the PAFs exhibit lowest unoccupied molecular orbitals close to those of phenyl‐C 61 ‐butyric acid methyl ester. Routine characterizations are correlated with DFT/B3LYP/6‐31G(d) to understand structural and electronic behaviours. It is expected that higher molecular weights may be obtained through comonomer variations and that this novel methodology will open a route to interesting materials for optoelectronics. © 2017 Society of Chemical Industry