title: Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines.
abstract: A series of scarce N-unsubstituted 2,5-diaryl fulleropyrrolidines as cis isomers could be prepared via the facile one-step reaction of [60]fullerene with N-unsubstituted arylmethanamines promoted by cheap and easily available ferric perchlorate. Nevertheless, the reaction of N-substituted arylmethanamines with [60]fullerene under the same conditions gave different experimental results. N-Methylbenzylamine formed N-methyl 2,5-diphenyl fulleropyrrolidine as a trans isomer, and N,N-dibenzylamine unexpectedly afforded the N-unsubstituted 2,5-diphenyl fulleropyrrolidine as a cis isomer. Intriguingly, high stereoselectivity for all 2,5-diaryl fulleropyrrolidines could be observed although both cis and trans isomers were possibly formed. N-Unsubstituted fulleropyrrolidine could be further converted to N-substituted fulleropyrrolidines under the assistance of an acid chloride or an isocyanate. A possible reaction pathway leading to 2,5-diaryl fulleropyrrolidines is also proposed.
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Ji-Long
authors: JL
authors: Shi
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Fa-Bao
authors: FB
authors: Li
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Xiao-Feng
authors: XF
authors: Zhang
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Jun
authors: J
authors: Wu
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Hong-Yu
authors: HY
authors: Zhang
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Jie
authors: J
authors: Peng
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Chun-Xiang
authors: CX
authors: Liu
authors: Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
authors: Li
authors: L
authors: Liu
authors: College of Chemistry and Chemical Engineering, Key Laboratory of Coordination Chemistry and Functional Materials in Universities of Shandong, Dezhou University , Dezhou 253023, People's Republic of China.
authors: Ping
authors: P
authors: Wu
authors: Key Laboratory of Novel Thin Film Solar Cells, Institute of Plasma Physics, Chinese Academy of Sciences , P.O. Box 1126, Hefei 230031, People's Republic of China.
authors: Jia-Xing
authors: JX
authors: Li