Synthesis and self-assembly properties of thiacrown-cyclized tetrathiafulvalene organogelators

A novel low-molecular-weight organogelator (1) based on thiacrown-cyclized tetrathiafulvalene has been synthesized through cross-coupling reaction of crown-fused 1,3-dithiole-2-one 3 and the thione 4 in the presence of triethyl phosphite. The molecular structure of 1 was fully characterized by nuclear magnetic resonance spectroscopy, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and infrared spectroscopy. Gel-forming-ability experiments showed that the gelator could only form an opaque gel in dimethyl sulfoxide by sonication. The xerogel morphology observed by scanning electron microscopy showed an amorphous wrinkled structure. The gel exhibited varied responses to various external stimuli, including temperature, chemical oxidation, anions, and Na+ ions.