Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 9, Issue 9, Pages 1922-1932Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200204459
Keywords
aggregation; donor-acceptor systems; gels; hydrogen bonding; pi-interactions
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A new class of alkyl-chain-appended pyrene derivatives 4-14 were synthesized and evaluated for their gelation abilities. Depending on the nature of the linking group, these compounds gelated a number of organic solvents, either in the presence or in the absence of the acceptor molecule 2,4,7-trinitrofluorenone (TNF). Compounds with ester, ether, or alkyl linkages gelated a number of hydroxylic and hydrocarbon solvents by means of a charge-transfer interaction with TNF, while compounds with amide, urethane and urea linkers formed gels on their own in a variety of solvents by means of pi-pi stacking and hydrogen-bonding interactions. The X-ray crystal structure of urethane (S)12 showed hydrogen-bonding and stacking features, as suggested by the model. The gels obtained were investigated by spectroscopic and electron microscopic techniques which provided structural insights.
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