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Rational Design of Nanofibers and Nanorings through Complementary Hydrogen‐Bonding Interactions of Functional π Systems
Author(s) -
Yagai Shiki,
Aonuma Hiroaki,
Kikkawa Yoshihiro,
Kubota Shun,
Karatsu Takashi,
Kitamura Akihide,
Mahesh Sankarapillai,
Ajayaghosh Ayyappanpillai
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000839
Subject(s) - hydrogen bond , melamine , nanofiber , conjugate , rational design , cyanuric acid , chemistry , self assembly , nanostructure , amide , dimer , ring (chemistry) , solvent , crystallography , polymer chemistry , materials science , stereochemistry , molecule , nanotechnology , organic chemistry , mathematical analysis , mathematics
A simple protocol to create nanofibers and ‐rings through a rational self‐assembly approach is described. Whereas the melamine–oligo( p ‐phenylenevinylene) conjugate 1 a self‐aggregates to form ill‐defined nanostructures, conjugate 1 b , which possesses an amide group as an additional interactive site, self‐aggregates to form 1D nanofibers that induce gelation of the solvent. AFM and XRD studies have shown that dimerization through the melamine–melamine hydrogen‐bonding interaction occurs only for 1 b . Upon complexation with 1/3 equivalents of cyanuric acid (CA), conjugate 1 a provides well‐defined, ring‐shaped nanostructures at micromolar concentrations, which open to form fibrous assemblies at submillimolar concentrations and organogels in the millimolar concentration range. Apparently, the enhanced aggregation ability of 1 a by CA is a consequence of columnar organization of the resulting discotic complex 1 a 3 ⋅ CA. In contrast, coaggregation of 1 b with CA does not provide well‐defined nanostructures, probably due to the interference of complementary hydrogen‐bonding interactions by the amide group.