Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 40, Pages 13450-13459Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8043322
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Funding
- National Science Foundation of China [20732007, 20621062, 20425208, 20572126, 20672137]
- National Basic Research Program [2007CB808000]
- Chinese Academy of Sciences [KJCX2-YW-H13]
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This paper reports a systematic study of the dynamic process for the self-assembly of chiral organogels from achiral hydrogen bonded hydrazide foldamers by induction of chiral glucose. Six foldamers incorporated with six decyl chains and two benzene, naphthalene, anthracene, or pyrene units at the ends are revealed to strongly gelate apolar and polar solvents, including alkanes, arenes, esters, alcohols, and 1,4-dioxane. The gels are characterized by UV-vis, fluorescent, XRD, SEM, and AFM methods, based on which a dislocated tail-to-tail stacking pattern is proposed. Addition of octylated glucose considerably enhances the capacity of the foldamers to gelate apolar solvents due to strong complexation. The complexation also causes unique dynamic helicity induction in the gels, which is studied systematically by circular dichroism. The results are treated with the Avrami theory according to a reported method (J. Am. Chem. Soc. 2005, 127, 4336), which suggests that the gelation involves a nucleation-elongation mechanism. In addition, the Sergeants and Soldiers effect in the gel phase is also revealed.
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