title: Novel fluorescent 1,8-naphthalimide derivatives containing thiophene and pyrazole moieties: synthesis by direct C-H arylation and evaluation of photophysical and electrochemical properties.
abstract: A series of novel 1,8-naphthalimide derivatives containing thiophene and pyrazole moities were synthesized by direct Pd-catalyzed C-H arylation and then characterized by (1)H NMR, (13)C NMR, MALDI-HRMS, and elementary analysis. The photophysical and electrochemical properties of the derivatives were also investigated. All compounds have green emission both in diluted CH2Cl2 solution and solid film. The cyclic voltammetry (CV) measurements showed that the target compounds had a lowest unoccupied molecular orbital (LUMO) range from -3.49 eV to -3.29 eV and a highest occupied molecular orbital (HOMO) range from -6.04 eV to -5.81 eV. Quantum chemical calculations were performed to obtain the optimized ground-state geometry as well as the spatial distributions of the HOMO, LUMO levels of the compounds.
authors.affiliation: Department of Pharmaceutics and Chemical Engineering, Taizhou University, Taizhou, Zhejiang 318000, PR China. Electronic address: zn_jin@tzc.edu.cn.
authors.forename: Zhengneng
authors.initials: Z
authors.lastname: Jin
authors.forename: Jiashou
authors.initials: J
authors.lastname: Wu
authors.forename: Chuanfeng
authors.initials: C
authors.lastname: Wang
authors.forename: Guoliang
authors.initials: G
authors.lastname: Dai
authors.forename: Shiyong
authors.initials: S
authors.lastname: Liu
authors.forename: Jianmei
authors.initials: J
authors.lastname: Lu
authors.forename: Huajiang
authors.initials: H
authors.lastname: Jiang
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D004563:Electrochemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D053644:Naphthalimides / Q000138:chemical synthesis* / Q000494:pharmacology*; D010777:Photochemistry; D011720:Pyrazoles / Q000737:chemistry*; D011789:Quantum Theory; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D053644:Naphthalimides; D011720:Pyrazoles; D013876:Thiophenes; C031280:pyrazole
keywords: C–H arylation; Fluorescence; Naphthalimide; Pyrazole; Thiophene