Coumarin derivatives, one of the organic fluorescent materials, are widely applied in many areas such as laser dyes, organic light emitting diodes (OLED), pharmaceuticals and bio/chemosensors, with the advantages of the large conjugated system and planar structure. In the coumarin analogs, which are polarity sensitive fluorophores, a shift to the red zone is observed in the case of π expansion at 3-positions and electron donor groups at 7-positions. The present article reports the synthesis of novel hybrid compounds (CD1-CD8) containing coumarin and benzodiazepine rings using ethyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate reagent and 1,2-diaminobenzene derivatives under optimized reaction conditions with PTSA catalyst. The structures of target compounds synthesized were characterized by FTIR, ¹HNMR, ¹³CNMR, HRMS and UV–Vis spectra. The effects of electron withdrawing and electron donor groups in the cyclocondensation reaction that takes place as regioselective were evaluated in detail. The substituent effects were investigated for n-π* and π-π* electronic transitions in UV–Vis Spectroscopy.

中文翻译：

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基于染料的含有香豆素和苯二氮杂环的新型杂化化合物的合成与表征

香豆素衍生物是有机荧光材料之一，具有大共轭体系和平面结构的优点，广泛应用于激光染料、有机发光二极管（OLED）、药物和生物/化学传感器等许多领域。在作为极性敏感荧光团的香豆素类似物中，在 3 位的 π 扩展和 7 位的电子供体基团的情况下观察到向红色区域的转移。本文报道了使用乙基 3-(7-(二乙氨基)-2-oxo-2 H )合成含有香豆素和苯二氮卓环的新型杂化化合物 ( CD1-CD8 )-chromen-3-yl)-3-氧代丙酸酯试剂和 1,2-二氨基苯衍生物在优化的反应条件下与 PTSA 催化剂。合成的目标化合物的结构通过FTIR、¹ HNMR、¹³ CNMR、HRMS和UV-Vis光谱表征。详细评估了吸电子基团和给电子基团在作为区域选择性发生的环缩合反应中的影响。在紫外-可见光谱中研究了 n-π* 和 π-π* 电子跃迁的取代基效应。