Pyrene-derived novel one- and two-component organogelators.
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 Xray 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.
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
P
P
Babu
N M
NM
Sangeetha
P
P
Vijaykumar
Uday
U
Maitra
Kari
K
Rissanen
A R
AR
Raju