Crystal-Packing Trends for a Series of 6,9,12,15,18-Pentaaryl-1-hydro[60]fullerenes

Journal Article · Mon Jun 11 00:00:00 EDT 2012 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201103400· OSTI ID:1081174

Kennedy, Robert D. ^[1]; Halim, Merissa ^[1]; Khan, Saeed I. ^[1]; Schwartz, Benjamin J. ^[1]; Tolbert, Sarah H. ^[1]; Rubin, Yves ^[1]

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1. Univ. of California, Los Angeles, CA (United States)

The relationship between the size of the substituents of aryl groups in a series of fifteen 6,9,12,15,18-pentaaryl-1-hydro[60]fullerenes and the solid-state structures and packing motifs of these compounds has been analyzed. Pentaarylfullerenes have a characteristic “badminton shuttlecock” shape that causes several derivatives to crystallize into columnar stacks. However, many pentaarylfullerenes form non-stacked structures with, for example, dimeric, layered, diamondoid, or feather-in-cavity relationships between molecules. Computational modeling gave a qualitative estimate of the best shape match between the ball and socket surfaces of each pentaarylfullerene. The best match was for pentaarylfullerenes with large, spherically shaped para-substituents on the aryl groups. The series of pentaarylfullerenes was characterized by single-crystal X-ray diffraction. A total of 34 crystal structures were obtained as various solvates and were categorized by their packing motifs.

• Research Organization: Energy Frontier Research Centers (EFRC) (United States). Molecularly Engineered Energy Materials (MEEM)
• Sponsoring Organization: USDOE
• DOE Contract Number: SC0001342
• OSTI ID: 1081174
• Journal Information: Chemistry - A European Journal, Vol. 18, Issue 24; Related Information: MEEM partners with University of California, Los Angeles (lead); University of California, Berkeley; Eastern Washington University; University of Kansas; National Renewable Energy Laboratory; ISSN 0947-6539
• Publisher: ChemPubSoc Europe
• Country of Publication: United States
• Language: English

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host–guest interactions
self-assembly
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stacking interactions