An organogelator named N-[3-(hydroxy)-4-(dodecyloxy)-benzoyl]-N’ (4’-nitro-benzoyl) hydrazide (D12) was synthesized. It could form stable gels in some of the tested organic solvent. SEM images revealed that the molecules self- assembled into fibrous aggregates in the xerogels. The X-ray diffraction analysis showed that the xerogel exhibited a layered structure. FT-IR studies confirmed that intermolecular hydrogen bonding between C=O and N-H groups was the major driving force for gelation of organic solvents. The gel exhibited gel-sol transition and color change upon addition of F - . An extended conjugated system formed through the phenyl group and a five-membered ring based on intramolecular hydro-gen bonding between the oxygen atom near the deprotonation nitrogen atom and the other NH, which is responsible for the dramatic color change upon addition of F - .
Sangeetha, N.M. and Maitra, U. (2005) Supramolecular Gels: Functions and Uses. Chemical Society Reviews, 34, 821-836. https://doi.org/10.1039/b417081b
Kim, T.H., Kim, D.G., Lee, M. and Lee, T.S. (2010) Synthesis of Reversible Fluorescent Organogel Containing 2-(2’-Hydroxyphenyl)Benzoxazole: Fluorescence Enhancement upon Gelation and Detecting Property for Nerve Gas Simulant. Tetrahedron, 66, 1667-1672. https://doi.org/10.1016/j.tet.2010.01.006
Skilling, K.J., Citossi, F., Bradshaw, T.D., Ashford, M., Kellam, B., and Marlow, M. (2013) Insights into Low Molecular Mass Organic Gelators: A Focus on Drug Delivery and Tissue Engineering Applications. Soft Matter, 10, 237-256. https://doi.org/10.1039/C3SM52244J
Miao, R., Peng, J. and Fang, Y. (2017) Molecular Gels as Intermediates in the Synthesis of Porous Materials and Fluorescent Films: Concepts and Applications. Langmuir, 33, 10419-10428. https://doi.org/10.1021/acs.langmuir.6b04655
Wang, Y., Xing, P., Lin, S., Ma, M., Yang, M., Zhang, Y., Wang, B. and Hao, A. (2016) Facile Stimuli-Responsive Transformation of Vesicle to Nanofiber to Supramolecular Gel via ω-Amino Acid-Based Dynamic Covalent Chemistry. Langmuir, 32, 10705-10711. https://doi.org/10.1021/acs.langmuir.6b02478
Busschaert, N., Caltagirone, C., Rossom, W.V. and Gale, P.A. (2015) Applications of Supramolecular Anion Recognition. Chemical Reviews, 115, 8038-8155. https://doi.org/10.1021/acs.chemrev.5b00099
Duan, P.F., Yanai, N., Nagatomi, H. and Kimizuka, N. (2015) Photon Up-conversion in Supramolecular Gel Matrixes: Spontaneous Accumulation of Light-Harvesting Donor-Acceptor Arrays in Nanofibers and Acquired Air Stability. Journal of American Chemical Society, 137, 1887-1894. https://doi.org/10.1021/ja511061h
Zhong, D.C., Liao, L.Q., Wang, K.J., Liu, H.J. and Luo, X.Z. (2015) Heat-Set Gels Formed from Easily Accessible Gelators of a Succinamic Acid Derivative (SAD) and a Primary Alkyl Amine (R-NH2). Soft Matter, 11, 6386-6392. https://doi.org/10.1039/C5SM01305D
He, N., Zhi, K.K., Yang, X., Zhao, H., Zhang, H., Wang, J. and Wang, Z. (2018) Self-Assembled Fibrillar Networks Induced by Two Methods: A New Unmodified Natural Product Gel. New Journal of Chemistry, 42, 14170-14178. https://doi.org/10.1039/C8NJ01302K
Reddy, S.M.M., Dorishetty, P., Augustine, G., Deshpande, A.P., Ayyadurai, N. and Shanmugam, G. (2017) A Low-Molecular-Weight Gelator Composed of Pyrene and Fluorene Moieties for Effective Charge Transfer in Supramolecular Ambidextrous Gel. Langmuir, 33, 13504-13514. https://doi.org/10.1021/acs.langmuir.7b03453
Zhou, Y., Zhang, J. and Yoon, J. (2014) Fluorescence and Colorimetric Chemosensors for Fluoride-Ion Detection. Chemical Reviews, 114, 5511-5571. https://doi.org/10.1021/cr400352m
Yu, X., Xie, D., Li, Y., Geng, L., Ren, J., Wang, T. and Pang, X. (2017) Photochromic Property of Naphthalimide Derivative: Selective and Visual F - Recognition by NSS Isomers Both in Solution and in a Self-Assembly Gel. Sensors and Actuators B, 251, 828-835. https://doi.org/10.1016/j.snb.2017.05.132
Lin, X., Zhang, Y., Chen, A., Zhang, B., Zhang, B. and Song, J. (2017) A Ferrocene-Based Organogel with Multi-Stimuli Properties and Applications in Naked-Eye Recognition of F - and Al 3+ . RSC Advances, 7, 37105-37111. https://doi.org/10.1039/C7RA06722D
Bai, B., Zhang, M., Wei, J., Yan, H., Wang, H., Wu, Y. and Li, M. (2016) Stimuli-Responsive Organogels Based on a Gelator of Hydrazide and Azobenzene Units Connected via a Flexible Central Spacer. Tetrahedron, 72, 5363-5368. https://doi.org/10.1016/j.tet.2016.07.025
Xu, Y.L., Li, C.T., Cao, Q.Y., Wang, B.Y. and Xie, Y. (2017) A Pyrenyl-Appended Organogel for Fluorescence Sensing of Anions. Dyes and Pigments, 139, 681-687. https://doi.org/10.1016/j.dyepig.2016.12.068
Shiraishi, Y., Maehara, H. and Hirai, T. (2009) Indole-Azadiene Conjugate as a Colorimetric and Fluorometric Probe for Selective Fluoride Ion Sensing. Organic Biomolecular Chemistry, 7, 2072-2076. https://doi.org/10.1039/b821466b
Bai, B., Mao, X., Wei, J., Wei, Z., Wang, H. and Li, M. (2015) Selective Anion-Responsive Organogel Based on a Gelator Containing Hydrazide and Azobenzene Units. Sensors Actuators B, 211, 268-273. https://doi.org/10.1016/j.snb.2015.01.111
Geng, L., Feng, G., Wang, S., Yu, X., Xu, Z., Zhen, X. and Wang, T. (2015) Fluoride-Responsive Organogel Containing Azobenzyl and Cholesterol Units. Journal of Fluorine Chemistry, 170, 24-28. https://doi.org/10.1016/j.jfluchem.2014.12.005
Zang, L., Shang, H., Wei, D. and Jiang, S. (2013) A Multi-Stimuli-Responsive Organogel Based on Salicylidene Schiff Base. Sensors Actuators B, 185, 389-397. https://doi.org/10.1016/j.snb.2013.05.022
Bai, B., Zhao, C., Wang, H., Ran, X., Wang, D. and Li, M. (2012) Columnar Mesophase from Non-Symmetrical Tapered Hydrazide Derivatives. Materials Chemistry and Physics, 133, 232-238. https://doi.org/10.1016/j.matchemphys.2012.01.015
Abdallah, D.J. and Weiss, R.G. (2000) n-Alkanes Gel n-Alkanes (and Many Other Organic Liquids). Langmuir, 16, 352-355. https://doi.org/10.1021/la990795r
Bai, B., Mao, X., Xi, Z., Ma, J., Lin, X., Wang, H.T. and Li, M. (2014) Liquid Crystalline Behaviour of Hydrazide Derivatives Containing Alkoxyazobenzene. Liquid Crystal, 41, 214-221. https://doi.org/10.1080/02678292.2013.847977
Zhang, P., Wang, H.T., Liu, H. and Li, M. (2010) Fluorescence-Enhanced Organogels and Mesomorphic Superstructure Based on Hydrazine Derivatives. Langmuir, 26, 10183-10190. https://doi.org/10.1021/la100325c
Wei, Z., Wei, J., Bai, B., Wang, H.T. and Li, M. (2015) Anion Response of Dimeric Hydrazide Derivatives: Dependence on the Nature of Terminal Substituents. Journal of Molecular Liquids, 204, 100-105. https://doi.org/10.1016/j.molliq.2015.01.049
Bai, B., Ma, J., Wei, J., Song, J., Wang, H.T. and Li, M. (2014) A Simple Structural Hydrazide-Based Gelator as a Fluoride Ion Colorimetric Sensor. Organic Biomolecular Chemistry, 12, 3478-3483. https://doi.org/10.1039/c4ob00056k