Hexa‐peri‐hexabenzocoronene with Different Acceptor Units for Tuning Optoelectronic Properties. Issue 19 (8th August 2016)

• Record Type: Journal Article
• Authors: Keerthi, Ashok; Hou, Ian Cheng‐Yi; Marszalek, Tomasz; Pisula, Wojciech; Baumgarten, Martin; Narita, Akimitsu
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 19(2016)
• Page Start: 2710
• Page End: 2714
• Publication Date: 2016-08-08
• Subjects: charge transfer -- dehydrogenation -- donor–acceptor systems -- graphene -- polycycles; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201600638
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: Hexa‐ peri ‐hexabenzocoronene (HBC)‐based donor–acceptor dyads were synthesized with three different acceptor units, through two pathways: 1) "pre‐functionalization" of monobromo‐substituted hexaphenylbenzene prior to the cyclodehydrogenation; and 2) "post‐functionalization" of monobromo‐substituted HBC after the cyclodehydrogenation. The HBC–acceptor dyads demonstrated varying degrees of intramolecular charge‐transfer interactions, depending on the attached acceptor units, which allowed tuning of their photophysical and optoelectronic properties, including the energy gaps. The two synthetic pathways described here can be complementary and potentially be applied for the synthesis of nanographene–acceptor dyads with larger aromatic cores, including one‐dimensionally extended graphene nanoribbons. Abstract : Give and take : Hexa‐ peri ‐hexabenzocoronene (HBC)‐based donor–acceptor dyads were synthesized with three different acceptor units, 9, 10‐anthraquinone (AQ ), naphthalene‐1, 8‐dicarboximide (NMI ), and perylene‐3, 4‐dicarboximide (PMI ). The three HBC–acceptor dyads demonstrated varying degrees of intramolecular charge‐transfer interactions, allowing tuning of their photophysical and optoelectronic properties.