Towards the synthesis of poly(azafulleroid)s: main chain fullerene oligomers for organic photovoltaic devices

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Bregadiolli, Bruna A. ; Ramanitra, Hasina H. ; Ferreira, Rodrigo Marques ; Corcoles, Laura ; Gomes, Milton S. ; Kang, Lauren ; Combe, Craig M. S. ; Silva, Hugo Santos ; Lavarda, Francisco C. ; Begue, Didier ; Dagron-Lartigau, Christine ; Rocco, Maria Luiza M. ; Luscombe, Christine K. ; Olivati, Clarissa A. ; Graeff, Carlos F. O. ; Hiorns, Roger C.

• Document type: Journal article
• Source: Polymer International; v. 66, n. 10, p. 1364-1371, OCT 2017.
• Web of Science Citations: 1

Abstract

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. (C) 2017 Society of Chemical Industry (AU)

• FAPESP's process: 11/02205-3 - Hybrid solar cell based on TiO2 nanoparticles
• Grantee: Bruna Andressa Bregadiolli
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)