Nicotinamide-based supergelator self-assembling via asymmetric hydrogen bonding NH OC and H Br pattern for reusable, moldable and self-healable nontoxic fuel gels
Author | Kasak, Peter |
Author | Hrobarik, Peter |
Author | Osicka, Josef |
Author | Solarikova, Dominika |
Author | Horvath, Branislav |
Author | Tkac, Jan |
Author | Sadasivuni, Kishor K. |
Author | AlMaadeed, Mariam A. |
Author | Miklase, Roman |
Available date | 2022-03-23T06:35:44Z |
Publication Date | 2021 |
Publication Name | Journal of Colloid and Interface Science |
Resource | Scopus |
Identifier | http://dx.doi.org/10.1016/j.jcis.2021.06.071 |
Abstract | Hypothesis Development of highly efficient low-molecular weight gelators (LMWGs) for safe energy storage materials is of great demand. Energy storage materials as fuel gels are often achieved by construction of hybrid organic frameworks capable of multiple noncovalent interactions in self-assembly, which allow tuning required properties at the molecular level by altering individual building blocks of the LMWG. However, LMWGs have limited rechargeable capability due to their chemical instability. Experiments We designed, synthesized and characterized a novel, bio-inspired chiral gemini amphiphile derivative 1 containing N-hexadecyl aliphatic tails from quaternized nicotinamide-based segment and bromide anion showing supergelation ability in water, alcohols, aprotic polar and aromatic solvents, with critical gel concentrations as low as 0.1 and 0.035 wt% in isopropanol and water, respectively. Findings Nanostructural architecture of the network depended on the solvent used and showed variations in size and shape of 1D nanofibers. Supergelation is attributed to a unique asymmetric NH⋯OC, H⋯Br− hydrogen bonding pattern between H-2 hydrogens from nicotinamide-based segment, amide functional groups from chiral trans-cyclohexane-1,2-diamide-based segment and bromide ions, supporting the intermolecular amide–amide interactions appearing across one strand of the self-assembly. Gels formed from 1 exhibit high stiffness, self-healing, moldable and colorable properties. In addition, isopropanol gels of 1 are attractive as reusable, shape-persistent non-toxic fuels maintaining the chemical structure with gelation efficiency for at least five consecutive burning cycles. |
Sponsor | This publication was jointly supported by Qatar University and Chemical Institute, Slovak Academy of Sciences Grant IRCC-2020-004 . The findings achieved herein are solely the work of the authors. This work was supported by the Slovak Research and Development Agency (grant no. APVV-17-0324 ) as well as by the Grant Agency of the Ministry of Education of the Slovak Republic (VEGA projects no. 1/0712/18 and 1/0145/20). P.H. also acknowledges the support from the European Union?s Horizon 2020 research and innovation programme under grant no. 810701 . J.O. acknowledges the Ministry of Education, Youth and Sports of the Czech Republic?DKRVO (RP/CPS/2020/003). Authors thank to Dr. Emil ?vajdlenka, Faculty of Pharmacy, Comenius University in Bratislava for HRMS measurements and Center for Advanced Materials and Gas Processing Center at Qatar University for support with facilities. The publication of this article was funded by the Qatar National Library. |
Language | en |
Publisher | Academic Press Inc. |
Subject | Circular dichroism DFT calculations Fuel gel Low-molecular weight gelators Nicotinamide derivative Supergelation |
Type | Article |
Pagination | 182-190 |
Volume Number | 603 |
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