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Crystal‐Packing Trends for a Series of 6,9,12,15,18‐Pentaaryl‐1‐hydro[60]fullerenes
Author(s) -
Kennedy Robert D.,
Halim Merissa,
Khan Saeed I.,
Schwartz Benjamin J.,
Tolbert Sarah H.,
Rubin Yves
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103400
Subject(s) - diamondoid , fullerene , crystallography , series (stratigraphy) , crystal (programming language) , molecule , crystal structure , close packing of equal spheres , solid state , materials science , aryl , chemistry , organic chemistry , geology , computer science , paleontology , alkyl , programming language
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.