Cyclic Aromatic Disulfide Oligomers:  Synthesis and Characterization

Abstract

A series of cyclic aromatic disulfide oligomers have been synthesized in high yields by catalytic oxidization of arenedithiols in DMAc. The aryl groups contain moieties such as ketone, sulfone, isopropylidene, ether, thioether, and phenylphosphine oxide groups. The cyclic aromatic disulfide oligomers have been analyzed by gradient HPLC, GPC, 1 H-NMR, MALDI-TOF-MS, DSC, and TGA methods. Repeating units up to 9 for some cyclic aromatic disulfide ketone oligomers have been confirmed by MALDI-TOF-MS. In general, these cyclic aromatic disulfide oligomers are soluble in common organic solvents and have sharp melting points. Cyclic disulfide ketone oligomers and cyclic disulfide sulfone oligomers have higher glass transition temperatures and melting points than their ether or thioether counterparts.

Synthesis and properties of polyimides from isomeric bis(dicarboxylphenylthio)diphenyl sulfone dianhydrides

“…It was prepared according to the procedure in the literature [26], mp 138-140 8C (literature [26], mp 137-139 8C).…”

Determination of cyclic structure for polydithiane using electrospray ionization mass spectrometry

“…9 Hay and coworkers have reported the ring-opening polymerization of aryl disulfides for the preparation of cyclic arylene sulfides. 10,11 The characterization of the cyclic oligomers with the repeating units ranging from 3 to 10 was carried out by MALDI-TOF-MS. The cyclic hexamer composed of the thio-1,4-phenylene unit was well confirmed in the MALDI mass spectra.…”

MP2 and DFT Calculations on Circulenes and an Attempt to Prepare the Second Lowest Benzolog, [4]Circulene

“…Treatment of 25 c with phosphorus pentachloride gave the pseudo-gem-disulfonyl chloride 26, which was characterised by its spectroscopic data (see Experimental Section) and X-ray structural analysis (see below). The reduction of 23 with tin dichloride [36] in ethanol furnished the oxygen-sensitive dithiol 23, which was also crystallised and investigated by X-ray structural analysis (see below).…”