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One Pot Synthesis of New Benzimidazole Derivatives with Exceptionally High Luminescence Quantum Efficiency
Current Organic Synthesis ( IF 1.8 ) Pub Date : 2024-01-21 , DOI: 10.2174/0115701794271985231219070212
Abraham Mensah 1 , Xin-Ye Liu 1 , Bing-Xiang Hu 1 , Ennin Vendish Kweku 1 , Fang-Ming Wang 1 , Li-Zhuang Chen 1 , Shao-Jun Zheng 1
Affiliation  

Aim and Objzectives: There are different approaches to the synthesis of benzimidazole. In this article, five new benzimidazole derivatives, BMPO, Me-BMPO, Di-MeBMPO, F-BMPO and Cl-BMPO where (BMPO=3-[(1H)-benzo[d]imidazol-2-yl]pyridin-2(1H)-one), have been prepared. Another study was carried out on luminescence properties and their potential applica-tions for the detection of transition metal ions. Materials and Methods: From the one-pot synthesis approach, all the derivatives of the benzim-idazole compounds were obtained. The compounds were characterized using HRMS, 1HNMR, 13CNMR, and X-ray crystallography. Herein, a mechanism has been deciphered by predicting the release of HCl(g). Results: All compounds showed a strong deep blue emission when dissolved in dimethylacetamide (DMA), with emission wavelengths at 423, 428, 435, 423, and 421 nm, and half-times of 3.64, 2.77, 2, 19, 3.42 and 3.52 ns, respectively. In addition, their emission quantum yields were deter-mined to be 72, 50, 42, 73 and 80%. Conclusion: Five new benzimidazole derivatives, BMPO, Me-BMPO, Di-MeBIPO, F-BIPO, and Cl-BIPO, have been successfully synthesized by the one-pot synthesis method, and their struc-tures are characterized and confirmed. The compounds exhibited exceptional luminescence by emitting a strong blue light in DMA with high fluorescence quantum yields between 42~80%.

中文翻译:

一锅法合成具有极高发光量子效率的新型苯并咪唑衍生物

目的和目标:苯并咪唑的合成有不同的方法。在本文中,五种新的苯并咪唑衍生物:BMPO、Me-BMPO、Di-MeBMPO、F-BMPO 和 Cl-BMPO 其中 (BMPO=3-[(1H)-苯并[d]咪唑-2-基]pyridin-2 (1H)-一),已准备好。另一项研究是关于发光特性及其在过渡金属离子检测中的潜在应用。材料与方法:采用一锅合成法,得到苯并咪唑类化合物的所有衍生物。使用 HRMS、1HNMR、13CNMR 和 X 射线晶体学对化合物进行了表征。在此,通过预测 HCl(g) 的释放,破译了一种机制。结果:所有化合物溶解在二甲基乙酰胺(DMA)中时均表现出强烈的深蓝色发射,发射波长分别为423、428、435、423和421 nm,半衰期为3.64、2.77、2、19、3.42和3.52分别是ns。此外,它们的发射量子产率确定为72%、50%、42%、73%和80%。结论:采用一锅法成功合成了BMPO、Me-BMPO、Di-MeBIPO、F-BIPO和Cl-BIPO 5种新型苯并咪唑衍生物,并对其结构进行了表征和确认。该化合物在DMA中发出强蓝光,表现出优异的发光性能,荧光量子产率高达42~80%。
更新日期:2024-01-21
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