TY - JOUR
T1 - Molecular programming of organogelators which can accept [60]fullerene by encapsulation
AU - Shirakawa, Michihiro
AU - Fujita, Norifumi
AU - Shimakoshi, Hisashi
AU - Hisaeda, Yoshio
AU - Shinkai, Seiji
N1 - Funding Information:
This work was partially supported by Grant-in-Aid for Young Scientists (B) (No. 16750122) and the 21st Century COE Program, ‘Functional Innovation of Molecular Informatics’ from the Ministry of Education, Culture, Science, Sports and Technology of Japan and JSPS fellowship (for M.S.) Authors would like to thank Ms. Okasaki of Kyushu University for FAB-MS (HR) measurements.
PY - 2006/2/27
Y1 - 2006/2/27
N2 - New porphyrin-based gelators bearing eight hydrogen-bond-forming amide groups at their periphery were synthesized. They acted as versatile gelators for aromatic solvents. SEM and TEM observations and X-ray crystallographic analysis established that they tend to aggregate into a two-dimensional sheet-like structure utilizing the intermolecular hydrogen-bonding interaction. In this structure the porphyrin-porphyrin π-π stacking interaction is not involved because of the energetically-predominant hydrogen-bonding interactions, keeping the space distance of 12.9 Å. Very interestingly, when C60 was added, the morphology was transformed to a one-dimensional fibrous structure, which can enjoy a porphyrin-C60-porphyrin interaction. This multicapsular structure having porphyrin-based compartments for hosting C 60 was further characterized by XRD, EPR of a Cu(II) analogue, and the theoretical calculation. Thus, this paper presents a new concept, 'molecular recognition in gel', which is effective for the weak host-guest interaction.
AB - New porphyrin-based gelators bearing eight hydrogen-bond-forming amide groups at their periphery were synthesized. They acted as versatile gelators for aromatic solvents. SEM and TEM observations and X-ray crystallographic analysis established that they tend to aggregate into a two-dimensional sheet-like structure utilizing the intermolecular hydrogen-bonding interaction. In this structure the porphyrin-porphyrin π-π stacking interaction is not involved because of the energetically-predominant hydrogen-bonding interactions, keeping the space distance of 12.9 Å. Very interestingly, when C60 was added, the morphology was transformed to a one-dimensional fibrous structure, which can enjoy a porphyrin-C60-porphyrin interaction. This multicapsular structure having porphyrin-based compartments for hosting C 60 was further characterized by XRD, EPR of a Cu(II) analogue, and the theoretical calculation. Thus, this paper presents a new concept, 'molecular recognition in gel', which is effective for the weak host-guest interaction.
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U2 - 10.1016/j.tet.2005.07.125
DO - 10.1016/j.tet.2005.07.125
M3 - Article
AN - SCOPUS:31944443188
SN - 0040-4020
VL - 62
SP - 2016
EP - 2024
JO - Tetrahedron
JF - Tetrahedron
IS - 9
ER -