Pyridine-containing versatile gelators for post-modification of gel tissues toward construction of novel porphyrin nanotubes

Sudip Malik, Shin ichiro Kawano, Norifumi Fujita, Seiji Shinkai

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7326-7333
Number of pages8
JournalTetrahedron
Volume63
Issue number31
DOIs
Publication statusPublished - Jul 30 2007

Fingerprint

Nanotubes
Porphyrins
Gels
Tissue
Fibers
Molecules
Metals
Cholesterol
Gelation
Coulomb interactions
Ultraviolet spectroscopy
Static Electricity
Transmission Electron Microscopy
Absorption spectroscopy
Confocal Microscopy
Tapes
Metal ions
Spectrum Analysis
Molecular Weight
Molecular weight

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Pyridine-containing versatile gelators for post-modification of gel tissues toward construction of novel porphyrin nanotubes. / Malik, Sudip; Kawano, Shin ichiro; Fujita, Norifumi; Shinkai, Seiji.

In: Tetrahedron, Vol. 63, No. 31, 30.07.2007, p. 7326-7333.

Research output: Contribution to journalArticle

Malik, Sudip ; Kawano, Shin ichiro ; Fujita, Norifumi ; Shinkai, Seiji. / Pyridine-containing versatile gelators for post-modification of gel tissues toward construction of novel porphyrin nanotubes. In: Tetrahedron. 2007 ; Vol. 63, No. 31. pp. 7326-7333.
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