Structural sensitivity of peptoid-based low molecular mass organogelator. (15th October 2016)

• Record Type: Journal Article
• Authors: Biswas, Goutam; Moon, Hyo Jung; Boratyński, Przemysław; Jeong, Byeongmoon; Kwon, Yong-Uk
• Is Part Of: Materials & design. Volume 108(2016)
• Page Start: 659
• Page End: 665
• Publication Date: 2016-10-15
• Subjects: H-bonding -- Low molecular mass organogelator -- Nanofibrous morphology -- Organogel -- Peptoid -- Self-assembly; Materials -- Periodicals; Engineering design -- Periodicals; Matériaux -- Périodiques; Conception technique -- Périodiques; Electronic journals; 620.11
• DOI: 10.1016/j.matdes.2016.07.059
• Languages: English
• ISSNs: 0264-1275

Abstract

Abstract: A new class of peptoid-based low molecular mass organogelators was prepared by the aza-Michael addition reaction. The gelation was observed only for tert -butyl group substituted peptoid in chlorinated solvents including chloroform, 1, 2-dichloroethane, and 1, 2-dichlorobenzene. Interestingly, the peptoids with methyl, ethyl, n -propyl, n -butyl, and isobutyl groups did not exhibit gelation, indicating unique structural sensitivity of organogelation. The compound reported here is one of the simplest low molecular mass organogelators prepared so far. The physical properties, spectral data, and ab initio calculation suggest that nanofibrous morphology developed through the intermolecular hydrogen bonding of peptoid molecules plays a crucial role in organogelation. This study provides insights in designing various peptoid-based small molecule organogelators, and suggests that a minute structural difference should affect the formation of organogels significantly. Graphical abstract: Highlights: A new class of peptoid-based low molecular mass organogelators (LMOGs) showed structural sensitivity in organogelation. The compound reported here is one of the simplest LMOGs prepared so far. The nanofibrous morphology by H-bonding plays a crucial role in organogelation. This study can provide insights in designing various peptoid-based LMOGs.