Bis-dithiano perylene diimide: synthesis and characterization of a novel ring system

• Published in: RSC advances Vol. 4; no. 5; pp. 2368 - 2373
• Main Authors: Cormier, Russell A, Gregg, Brian A
• Format: Journal Article
• Language: English
• Published: 01.01.2014
• Subjects: Diimide
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/c3ra44872j

We report the transformation of a 1,7-dibromo perylene diimide into a 1,6,7,12-tetrasulfur-substituted expanded ring system at room temperature in high yield. The resulting bis-dithiano perylene diimide completes the series of five sulfur-annulated perylene ring systems, the first four of which are known. We describe the synthesis and characterization of the title compound, PS 4 , and other sulfur-annulated species formed under slightly different conditions. Optical and electrochemical data of both solution and solid films of this compound are reported. At slow scan rate a film of PS 4 self-organizes, rearranging its structure to accommodate its changing oxidation state. PS 4 is a lightly n-doped semiconductor in inert atmosphere (conductivity, σ = 4.6 × 10 −6 S cm −1 ) that becomes compensated in air ( σ = 2.4 × 10 −9 S cm −1 ) to an unusual, almost intrinsic (undoped) state. The properties of PS 4 suggest applications in organic electronics. The first bis-dithiano perylene diimide is synthesized and its optoelectronic properties characterized.