Benzimidazole derivatives: synthesis, physical properties, and n-type semiconducting properties

Autor:	Nina A. Esipenko, Daisuke Kumaki, Masashi Mamada, Pavel Anzenbacher, Cesar Perez-Bolivar, Shizuo Tokito
Rok vydání:	2014
Předmět:	Benzimidazole Organic Chemistry Heteroatom General Chemistry Photochemistry Catalysis Indium tin oxide chemistry.chemical_compound Crystallinity chemistry Diamine Physical chemistry Sublimation (phase transition) Cyclic voltammetry Naphthalene
Zdroj:	Chemistry (Weinheim an der Bergstrasse, Germany). 20(37)
ISSN:	1521-3765
Popis:	A series of new benzimidazole derivatives were synthesized by the solid-state condensation and direct sublimation (SSC-DS) method and their physical properties were investigated. The reaction yields and product stability were significantly affected by the identity of the diamine and anhydride substituents. On the other hand, the substituents of the benzimidazole ring allowed fine tuning of the emission maxima, fluorescence quantum yields, and redox potentials. The HOMO-LUMO levels were estimated by cyclic voltammetry in film on indium tin oxide (ITO) and compared with values obtained by other methods. The described benzimidazoles showed high crystallinity, which is attributed to a high planarity and interactions between carbon and heteroatoms. These compounds showed n-type semiconducting behavior in organic field-effect transistors (OFETs). Optimized devices for fluorinated NTCBI (naphthalene tetracarboxylic bisbenzimidazole) showed respectable electron mobilities of ∼10(-2) cm(2) V(-1) s(-1) .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a6f1f7a6408f6a9a4adb005eb67522b8 https://pubmed.ncbi.nlm.nih.gov/25079856 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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