Synthesis and Self‐Assembly of Novel s‐Tetrazine‐Based Gelator

Abstract

The design, synthesis and self‐assembly of new symmetrical 3,6‐bis(4‐(3,4,5‐tris(dodecyloxy)benzoate)phenyl)‐1,2,4,5‐tetrazine were described. The novel gelator, sym‐tetrazine, was prepared by addition reaction of 4‐cyanophenol with hydrazine monohydrate followed by oxidation reaction to afford the corresponding 3,6‐bis(4‐hydroxyphenyl)‐1,2,4,5‐tetrazine which was then subjected to esterification reaction with 3,4,5‐tris(dodecyloxy)benzoic acid. The chemical structure of the sym‐tetrazine gelator was confirmed by elemental analysis, fourier‐transform infrared spectroscopy (FT‐IR), and nuclear magnetic resonance (1H‐ and 13C‐NMR) spectral measurements. It was confirmed to exhibit relatively strong gelation ability to produce supramolecular assemblies in several polar alcoholic organic solvents, such as butanol, octanol, and 1,6‐dihydroxyhexane. The π‐π stacking and van der Waals mediated self‐assembly of tetrazine‐based organogelator were studied by scanning electron microscopy images of the xerogel to reveal that the obtained organogel consists of fibrillar aggregates. Investigation of FT‐IR and concentration‐dependent 1H‐NMR spectra confirm that the intermolecular van der Waals interactions and π‐π stacking were the key driving forces for self‐assembly during gelation process of s‐tetrazine molecules.

A review on synthesis of nitrogen-containing heterocyclic dyes for textile fibers - Part 2: Fused heterocycles

“…Dyes have been used as natural and synthetic products for a variety of applications, such as inkjet printing, plastics, textile coloration, adhesives, beverages, ceramics, photography, cosmetics, foodstuff, optoelectronics, coatings, sensors, xerography, constructions and biomedical applications [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Heteroaromatic compounds have been used in various fields of life sciences and technology [15][16][17][18][19][20][21]. Numerous of heterocyclic dyes are now commercialized to produce a full range of dyestuffs especially for textile coloration.…”

Photochromic and fluorescent ink using photoluminescent strontium aluminate pigment and screen printing towards anticounterfeiting documents

“…Smart chromic materials have the capability to be responsive to one or more external stimuli, such as heat, pH, light, solvent polarity, and electricity. [46][47][48][49][50][51][52][53][54][55][56][57][58][59][60] In this study, we developed a simple method to produce smart coating with the ability to respond to light. The long-lasting phosphorescence formula was prepared using several components including resins, lanthanide-doped strontium aluminate phosphor at different total contents (0.01, 0.05, 0.1, 0.25 and 0.5 wt%), alkali, mineral oil, and a dryer.…”

Hydrazone‐Based Supramolecular Organogel for Selective Chromogenic Detection of Organophosphorus Nerve Agent Mimic

“…There are different supramolecular structures that can be created by the self‐assembly of fibrillated networks, such as nanoribbons, nanorods and nanofibers [31–33] . To generate those types of self‐assembled structural networks, it has been significant to manage the intermolecular bonding through which the molecular units self‐assemble into higher order supramolecular architectures avoiding the transition to a dense crystal [34] . Stimuli‐responsive organogelators have lately attracted attention owing to their possible utilization in various fields, such as capture and removal of pollutants, soft materials for drug delivery and reconstructing medicines in tissue engineering [35–37] …”

“…[31][32][33] To generate those types of self-assembled structural networks, it has been significant to manage the intermolecular bonding through which the molecular units self-assemble into higher order supramolecular architectures avoiding the transition to a dense crystal. [34] Stimuli-responsive organogelators have lately attracted attention owing to their possible utilization in various fields, such as capture and removal of pollutants, soft materials for drug delivery and reconstructing medicines in tissue engineering. [35][36][37] Several structural models of low molecular mass organogelators have been described recently in literature.…”