One-step synthesis, characterization and X-ray analysis of benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-ones

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) .

show abstract

Benzimidazole Derivatives: Synthesis, Physical Properties, and n‐Type Semiconducting Properties

Mamada

Pérez‐Bolívar

Kumaki

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Synthesis, isolation and characterisation of fluorinated‐benzimidazoisoquinoline regioisomers

Lim

Pierens

Bernhardt

et al. 2021

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

A pair of novel fluorinated-benzimidazoisoquinoline regioisomers was synthesised and isolated. Initial structural characterisation and identification employed 1D proton, 1D carbon, correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), and heteronuclear multiple bond correlation (HMBC) nuclear magnetic resonance spectroscopy and mass spectrometry. However, the fluorinated regioisomers could not be differentiated using nuclear magnetic resonance (NMR) alone. Density functional theory calculations and single-crystal X-ray diffraction experiments were used to completely characterise and identify the compounds.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

One-step synthesis, characterization and X-ray analysis of benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-ones

Cited by 2 publications

References 29 publications

Benzimidazole Derivatives: Synthesis, Physical Properties, and n‐Type Semiconducting Properties

Benzimidazole Derivatives: Synthesis, Physical Properties, and n‐Type Semiconducting Properties

Synthesis, isolation and characterisation of fluorinated‐benzimidazoisoquinoline regioisomers

Contact Info

Product

Resources

About