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Effect of Hydrophobicity on the Self-Assembly Behavior of Urea Benzene Derivatives in Aqueous Solution

Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-Ku, Fukuoka 812-8582, Japan
Faculty of Pharmaceutical Sciences, Showa Pharmaceutical University, Machida 194-8543, Japan
PRESTO, Japan Science and Technology Agency, Kawaguchi 332-0012, Japan
Author to whom correspondence should be addressed.
Appl. Sci. 2018, 8(7), 1080;
Received: 10 June 2018 / Revised: 27 June 2018 / Accepted: 2 July 2018 / Published: 3 July 2018
(This article belongs to the Special Issue Heat Transfer across Nanoparticles)
PDF [2703 KB, uploaded 3 July 2018]


Urea benzene derivatives (UBD) with amphiphilic side chains showed self-assembly behavior in aqueous solution to form nanoparticles ~100 nm in size. Subsequent thermal treatment led to additional self-assembly of the nanoparticles due to dehydration of the amphiphilic side chains, producing microparticles. This self-assembly process was accompanied by a lower critical solution temperature (LCST) behavior, as revealed by the abrupt decrease in solution transmittance. In this study, three UBD (UBD-13) with different lengths of the alkyl segment in the amphiphilic side chain (namely, hexyl, heptyl, and octyl, respectively) were prepared to investigate the self-assembly behavior in aqueous solution. UBD-13 formed identical nanoparticles, with sizes in the 10~80 nm range but with different LCST values in the order 3 < 2 < 1. These results suggest a relationship between the hydrophobicity and the self-assembly behavior of UBD. View Full-Text
Keywords: nanoparticles; LCST; alkyl urea benzene framework; self-assembly nanoparticles; LCST; alkyl urea benzene framework; self-assembly

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Okamoto, Y.; Morishita, K.; Fuchi, Y.; Kobayashi, S.; Karasawa, S. Effect of Hydrophobicity on the Self-Assembly Behavior of Urea Benzene Derivatives in Aqueous Solution. Appl. Sci. 2018, 8, 1080.

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