Formation of High-Aspect-Ratio Helical Nanorods via Chiral Self-Assembly of Fullerodendrimers.
Two novel, asymmetric methanofullerenes are presented, which self-assemble in cyclohexane upon thermal cycling to 80 °C. We show that, through the introduction of a dipeptide sequence to one terminus of the dendritic methanofullerene, it is possible to transform the assembly behavior of these molecules from poorly formed aggregates to high-aspect-ratio nanorods. These nanorods have diameters of 3.76 ± 0.52 nm and appear to be composed of interwoven helices of dendritic fullerenes. As evidenced by circular dichroism, the helicity is characterized by a preferential handedness of assembly, which is imparted by the dipeptide moiety.
†Department of Chemical Engineering, §Department of Chemistry, and ‡Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Andrew J
AJ
Hilmer
†Department of Chemical Engineering, §Department of Chemistry, and ‡Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Darin O
DO
Bellisario
†Department of Chemical Engineering, §Department of Chemistry, and ‡Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Steven
S
Shimizu
†Department of Chemical Engineering, §Department of Chemistry, and ‡Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Thomas P
TP
McNicholas
†Department of Chemical Engineering, §Department of Chemistry, and ‡Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Qing Hua
QH
Wang
†Department of Chemical Engineering, §Department of Chemistry, and ‡Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Scott A
SA
Speakman
†Department of Chemical Engineering, §Department of Chemistry, and ‡Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Michael S
MS
Strano
Bingel addition; benzyl dendron; fullerene; methanofullerene; nanorod; self-assembly