TY - JOUR
T1 - Symmetry-aligned supramolecular encapsulation of C60
T2 - [C60 ⊂ (L)2], L =p-benzylcalix[5]arene or p-benzylhexahomooxacalix[3]arene
AU - Atwood, Jerry L.
AU - Barbour, Leonard J.
AU - Nichols, Peter J.
AU - Raston, Colin L.
AU - Sandoval, Christian A.
PY - 1999/12/1
Y1 - 1999/12/1
N2 - p-Benzylcalix[5]arene (1) or p-benzylhexahomooxacalix[3]arene (2) form 2:1 complexes with C60 in solutions of the fullerene or fullerite in toluene to give [C60 ⊂ (1)2] · 8toluene and [C60 ⊂ (2)2], respectively. In both structures the fullerene is shrouded by two staggered, trans-disposed, host molecules. These host calixarenes adopt a cone conformation and the benzyl groups are either dangling ([C60 ⊂ (1)2] · 8toluene) or they are positioned edge-on to the fullerene ([C60 ⊂ (2)2]). The alignment of the symmetry axis of the calixarene, C5 or C3, respectively, with the same symmetry element of C60 highlights the importance of symmetry matching in the design of host molecules for fullerenes, as it maximises the number of points of contact and the efficiency of the π⋯π interactions. Two host-guest associations for 1 and 2 with C60 are evident in solutions in toluene. The new oxacalix[3]arene 2 crystallises with chloroform as the 1:1 complex [CHCl3 ⊂ (2)].
AB - p-Benzylcalix[5]arene (1) or p-benzylhexahomooxacalix[3]arene (2) form 2:1 complexes with C60 in solutions of the fullerene or fullerite in toluene to give [C60 ⊂ (1)2] · 8toluene and [C60 ⊂ (2)2], respectively. In both structures the fullerene is shrouded by two staggered, trans-disposed, host molecules. These host calixarenes adopt a cone conformation and the benzyl groups are either dangling ([C60 ⊂ (1)2] · 8toluene) or they are positioned edge-on to the fullerene ([C60 ⊂ (2)2]). The alignment of the symmetry axis of the calixarene, C5 or C3, respectively, with the same symmetry element of C60 highlights the importance of symmetry matching in the design of host molecules for fullerenes, as it maximises the number of points of contact and the efficiency of the π⋯π interactions. Two host-guest associations for 1 and 2 with C60 are evident in solutions in toluene. The new oxacalix[3]arene 2 crystallises with chloroform as the 1:1 complex [CHCl3 ⊂ (2)].
KW - Calixarenes
KW - Fullerenes
KW - Host-guest chemistry
KW - Inclusion compounds
KW - Supramolecular chemistry
UR - http://www.scopus.com/inward/record.url?scp=0032987594&partnerID=8YFLogxK
U2 - 10.1002/(SICI)1521-3765(19990301)5:3<990::AID-CHEM990>3.0.CO;2-4
DO - 10.1002/(SICI)1521-3765(19990301)5:3<990::AID-CHEM990>3.0.CO;2-4
M3 - Article
AN - SCOPUS:0032987594
SN - 0947-6539
VL - 5
SP - 990
EP - 996
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 3
ER -