Journal
TETRAHEDRON LETTERS
Volume 43, Issue 20, Pages 3751-3755Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)00541-5
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A novel porphyrin (1b) bearing four urea groups at its periphery was synthesized. This compound tends to aggregate into one-dimensional direction, resulting in an organogel phase in anisole and diphenyl ether solvents. The gel can be formed even at 0.125 wt/vol% in anisole and the sol-gel phase transition temperatures (T-gel) are as high as 120 140degreesC, indicating that 1b acts as an excellent gelator for these specific solvents. The spectroscopic studies and electron-micrographic observations support the view that the pi-pi stacking interaction among porphyrin moieties and the hydrogen-bonding interaction among urea moieties operate synergistically to give rise to a stable one-dimensional aggregate structure indispensable for gel formation. Further interestingly, chiral urea derivatives are bound to this aggregate to twist it in a chiral manner. This is a unique example for a rationally-designed organogelator including a porphyrin core and urea peripheral groups. (C) 2002 Elsevier Science Ltd. All rights reserved.
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