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Synthesis and Self‐Assembly of Novel s ‐Tetrazine‐Based Gelator
Author(s) -
Khattab Tawfik A.
Publication year - 2018
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201800009
Subject(s) - tetrazine , chemistry , van der waals force , supramolecular chemistry , stacking , intermolecular force , self assembly , infrared spectroscopy , pyridazine , crystallography , molecule , proton nmr , polymer chemistry , stereochemistry , organic chemistry
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 ( 1 H‐ and 13 C‐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 1 H‐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.