TY - JOUR
T1 - Pyridine-containing versatile gelators for post-modification of gel tissues toward construction of novel porphyrin nanotubes
AU - Malik, Sudip
AU - Kawano, Shin ichiro
AU - Fujita, Norifumi
AU - Shinkai, Seiji
N1 - Funding Information:
We deeply thank Ms. Eri Okazaki and Prof. Fumito Tani for HRMS measurements. Financial support was provided by Grant-in-Aid (Nos. 15105004, 16750122, and 18033040) and 21st Century COE Project, Functional Innovation of Molecular Informatics from the MEXT and JSPS fellowship for S.M. and S.-i.K.
PY - 2007/7/30
Y1 - 2007/7/30
N2 - Low molecular weight gelators have recently been used as a template to construct novel kind of composite materials of different shape or structures such as helix, fibers, tape or tube through the electrostatic interaction between gelators and the intermediate molecules. In this article, we intricately apply the non-electrostatic interaction between gelator and fluorescent molecules to fabricate the gel fibers. To achieve our goal, we have intentionally designed pyridine containing cholesterol-based gelators 1-3 by keeping one thing in our mind that during the formation of the stacking column the pyridine moieties will be arranged like a spiral staircase around the cholesterol column. The gelation properties of these three gelators are tested in different solvents including sublimable solvents like naphthalene and the gelator 1 has emerged as a 'supergelator'. The morphologies strongly depend on the process of solvent removal from the gel state and the stabilities of gel have been tuned by the added metal ions like Ag(I) by using metal-ligand interaction. Lastly, we have decorated the gel fibers obtained from gelator 1 with fluorescent molecules like tetraphenyl porphyrin Zn(II) [4·H and 4·Zn] having photopolymerizable unit at the end of tether groups and the modified fibers are well characterized by UV-vis absorption spectroscopy, confocal laser scanning microscopy as well as transmission electron microscopy. This is a novel example of decoration of gel fibers with fluorescent molecules and the process will offer an alternate application in photochemical and electrochemical devices.
AB - Low molecular weight gelators have recently been used as a template to construct novel kind of composite materials of different shape or structures such as helix, fibers, tape or tube through the electrostatic interaction between gelators and the intermediate molecules. In this article, we intricately apply the non-electrostatic interaction between gelator and fluorescent molecules to fabricate the gel fibers. To achieve our goal, we have intentionally designed pyridine containing cholesterol-based gelators 1-3 by keeping one thing in our mind that during the formation of the stacking column the pyridine moieties will be arranged like a spiral staircase around the cholesterol column. The gelation properties of these three gelators are tested in different solvents including sublimable solvents like naphthalene and the gelator 1 has emerged as a 'supergelator'. The morphologies strongly depend on the process of solvent removal from the gel state and the stabilities of gel have been tuned by the added metal ions like Ag(I) by using metal-ligand interaction. Lastly, we have decorated the gel fibers obtained from gelator 1 with fluorescent molecules like tetraphenyl porphyrin Zn(II) [4·H and 4·Zn] having photopolymerizable unit at the end of tether groups and the modified fibers are well characterized by UV-vis absorption spectroscopy, confocal laser scanning microscopy as well as transmission electron microscopy. This is a novel example of decoration of gel fibers with fluorescent molecules and the process will offer an alternate application in photochemical and electrochemical devices.
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U2 - 10.1016/j.tet.2007.05.027
DO - 10.1016/j.tet.2007.05.027
M3 - Article
AN - SCOPUS:34250617483
SN - 0040-4020
VL - 63
SP - 7326
EP - 7333
JO - Tetrahedron
JF - Tetrahedron
IS - 31
ER -