Practical, high-yield synthesis of thiol-terminated diacetylenes for formation of conductive monolayers. Issue 40 (3rd October 2018)

• Record Type: Journal Article
• Authors: Bhupathiraju, N.V.S. Dinesh K.; Sayeedi, Muntasir; Rizvi, Waqar; Singh, Sunaina; Batteas, James D.; Michael Drain, Charles
• Is Part Of: Tetrahedron letters. Volume 59:Issue 40(2018)
• Page Start: 3629
• Page End: 3631
• Publication Date: 2018-10-03
• Subjects: Conjugated diacetylene -- Self-assembled monolayer -- Conductive monolayer -- Photonics; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.08.057
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The synthesis of thiol-terminated diacetylenes reported herein proceeds in 75–80% overall yields. Used sequential 'acetylene zipper' reaction, a Sonagashira coupling procedure for diactylene formation. Thioacetate product allows long term storage without resorting to using the disulfides. Abstract: Self-assembled monolayers of thiol terminated conjugated diacetylenes can be cross-linked using ultraviolet light to form highly conjugated polydiacetylenic conductive monolayers [1]; however, the reported syntheses of the diacetylene monomers present numerous problems that prevent the wide spread application of these in functional materials. We report a redesigned four-step synthesis that proceeds in 75–80% overall yields and allows gram scale production of an array of thiol terminated conjugated diacetylenes, thereby allowing examination and application of these low-dimensional conductive materials.