Novel fluorescent 1,8-naphthalimide derivatives containing thiophene and pyrazole moieties: Synthesis by direct C-H arylation and evaluation of photophysical and electrochemical properties

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• 作者：Zhengneng Jin ; Jiashou Wu ; Chuanfeng Wang ; Guoliang Dai ; Shiyong Liu ; Jianmei Lu ; Huajiang Jiang
• 关键词：Naphthalimide ; Thiophene ; Pyrazole ; C&ndash ; H arylation ; Fluorescence
• 刊名：Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
• 出版年：3 January, 2014
• 年：2014
• 卷：117
• 期：Complete
• 页码：527-534
• 全文大小：2281 K

文摘

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 ¹H NMR, ¹³C 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 鈭?.49 eV to 鈭?.29 eV and a highest occupied molecular orbital (HOMO) range from 鈭?.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.