Synthesis of 9, 10‐Dimethyl‐2, 3, 6, 7‐Anthracenetetra(thioacetate) and Benzenepentathiol; Improved Syntheses of 1, 2, 4, 5‐Benzenetetra(thioacetate) and Benzenehexathiol. Issue 10 (4th July 2016)

• Record Type: Journal Article
• Authors: Hu, Huaiyuan; Singh, Mayank Pratap; Baghel, Garima Singh; Dye, Gregory W.; Gerlach, Deidra L.; Vaid, Thomas P.
• Is Part Of: ChemistrySelect. Volume 1:Issue 10(2016)
• Page Start: 2163
• Page End: 2166
• Publication Date: 2016-07-04
• Subjects: Benezenepolythiols -- anthracenetetrathiol -- molecular electronics; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201600454
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A synthesis is reported for 9, 10‐dimethyl‐2, 3, 6, 7‐anthracenetetra(thioacetate), an anthracenetetrathiol derivative that may find use in molecular electronics and conducting metal‐organic frameworks (MOFs). The easily accessible 2, 3, 6, 7‐tetrahydroxy‐9, 10‐dimethylanthracene was treated with 2‐(4‐pyridyl)ethanethiol in molten p ‐toluenesulfonic acid to yield the tetra(thioether), which was methylated and then deprotected with triethylamine in the presence of acetic anhydride to yield 9, 10‐dimethyl‐2, 3, 6, 7‐anthracenetetra(thioacetate), a protected form of the tetrathiol. Separately, the first synthesis of benzenepentathiol and streamlined syntheses of 1, 2, 4, 5‐benzenetetra(thioacetate) and benzenehexathiol are reported. Abstract : An air‐stable anthracenetetrathiol derivative 9, 10‐dimethyl‐2, 3, 6, 7‐anthracenetetra(thioacetate) was prepared and characterized. Separately, the first synthesis of benzenepentathiol and streamlined syntheses of 1, 2, 4, 5‐benzenetetra(thioacetate) and benzenehexathiol are reported.