Derivatizing Tribenzothiophene‐Fused Hexa‐peri‐hexabenzocoronenes with Tunable Optoelectronic Properties. Issue 15 (15th July 2016)

• Record Type: Journal Article
• Authors: Liu, Yi; Marszalek, Tomasz; Müllen, Klaus; Pisula, Wojciech; Feng, Xinliang
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 15(2016)
• Page Start: 2107
• Page End: 2112
• Publication Date: 2016-07-15
• Subjects: benzothiophene -- helical packing -- hexa-peri-hexabenzocoronenes -- oxidation -- thiophene-S, S-dioxide; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201600753
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: A series of trisbenzothieno[1, 2:7, 8:13, 14]hexa‐ peri ‐hexabenzocoronenes were synthesized and characterized by a combination of NMR, 2D NMR, MALDI‐TOF MS, UV/Vis absorption spectroscopy, and 2D‐WAXS measurement. By structural modulation like decoration of electro‐donating alkoxyl chain, and conversion from an electron‐rich thiophene ring into an electron‐poor thiophene‐ S, S ‐dioxide moiety, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels of the hexabenzocoronenes derivatives can be effectively tuned which is further verified by the DFT calculations and cyclic voltammetry. Abstract : Rich thiophene, poor thiophene : A series of trisbenzothieno[1, 2:7, 8:13, 14]hexa‐ peri ‐hexabenzocoronenes were synthesized. Their optoelectronic properties and supramolecular behavior can be effectively tuned through the attachment of electron‐donating alkoxy chains or the conversion of electron‐rich thiophene rings to electron‐poor thiophene‐ S, S ‐dioxide moieties.