Synthesis of bis[N-(p-aryl)-carbamoyloxy]alkanes as new low-molecular weight organogelators

DEMİR ORDU Ö., ŞİMŞİR H. , Alper K.

TETRAHEDRON, cilt.71, ss.1529-1539, 2015 (SCI İndekslerine Giren Dergi)

  • Cilt numarası: 71 Konu: 10
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.tet.2015.01.042
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayısı: ss.1529-1539

Özet

A series of bis-carbamate-based low-molecular-weight organogelators were synthesized, and their structure property relationships with respect to their gelation abilities in organic solvents were investigated. The self-aggregation behavior of the thermoreversible organogels was investigated by FTIR, temperature-dependent NMR, and SEM studies. The results revealed that the self-assembly into fibrous structures is driven by hydrogen bonding, it it stacking, and hydrophobic interactions. It was found that para-aryl substitution and the number of methylene units connecting two carbamate groups had a significant influence on gelation. The effect of temperature on gel formation was also investigated for all compounds. The most interesting feature was observed for p-hexyl derivative, which gels at -18 degrees C but not room temperature. Furthermore, thermal properties of the gels were studied by dropping ball experiments and DSC. para-Alkoxyphenyl derivatives were also found to be good organogelators for olive oil, sunflower oil, corn oil, and ethyl laurate, isopropyl myristate, n-butyl palmitate. (C) 2015 Elsevier Ltd. All rights reserved.