The regioselectivity and synthetic mechanism of 1,2-benzimidazole squaraines: combined experimental and theoretical studies

被引:7
作者
Xia, Guomin [1 ]
Wu, Zhiwei [1 ]
Yuan, Yanli [1 ]
Wang, Hongming [1 ]
机构
[1] Nanchang Univ, Dept Chem, Inst Adv Study, Nanchang 330031, Peoples R China
基金
中国国家自然科学基金;
关键词
SQUARIC ACID; SOLAR-CELLS; EFFICIENT; DERIVATIVES; INHIBITORS; DYES;
D O I
10.1039/c3ra43608j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this paper, a synthetic method to produce 1,2-benzimidazole squaraines with a yield of up to 89% is developed. It is found that both strong organic and inorganic bases have a satisfactory catalytic activity for this reaction. Theoretical studies provide detailed explanations for the 1,2 versus 1,3 condensation regiochemistry of the squaraines. The experimental and theoretical studies agree well with each other, paving a practical way to efficiently synthesize 1,2-squaraines.
引用
收藏
页码:18055 / 18061
页数:7
相关论文
共 50 条
[31]   Metal complexes of benzimidazole-derived as potential anti-cancer agents: synthesis, characterization, combined experimental and computational studies [J].
Nguyen, Van-Thanh ;
Huynh, Thi-Kim-Chi ;
Ho, Gia-Thien-Thanh ;
Nguyen, Thi-Hong-An ;
Le Anh Nguyen, Thi ;
Dao, Duy Quang ;
Mai, Tam V. T. ;
Huynh, Lam K. ;
Hoang, Thi-Kim-Dung .
ROYAL SOCIETY OPEN SCIENCE, 2022, 9 (09)
[32]   Experimental and Theoretical Studies of Action Mechanism of an Octadecylamine-based Molecular Assembly on Mild Steel [J].
Ma Yucong ;
Fan Baomin ;
Hao Hua ;
Lu Jinyu ;
Feng Yunhao ;
Yang Biao .
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2019, 40 (01) :96-107
[33]   Synthetic studies toward 1,2-dioxanes as precursors of potential endoperoxide-containing antimalarials [J].
Gemma, Sandra ;
Marti, Francesc ;
Gabellieri, Emanuele ;
Campiani, Giuseppe ;
Novellino, Ettore ;
Butini, Stefania .
TETRAHEDRON LETTERS, 2009, 50 (41) :5719-5722
[34]   Interaction of Multimicrobial Synthetic Inhibitor 1,2-Bis(2-Benzimidazolyl)-1,2-Ethanediol with Serum Albumin: Spectroscopic and Computational Studies [J].
Kamtekar, Nayana ;
Pandey, Anita ;
Agrawal, Neeraj ;
Pissurlenkar, Raghuvir R. S. ;
Borana, Mohanish ;
Ahmad, Basir .
PLOS ONE, 2013, 8 (01)
[35]   Sustainable porous graphene/Co-MOF for the removal of water pollutants: Combined theoretical and experimental studies [J].
Bano, Zahira ;
Akram, Muhammad ;
Ali, Naveed Zafar ;
Khan, Muhammad Usman ;
Wang, Fengyun ;
Li, Linrui ;
Xia, Mingzhu .
JOURNAL OF WATER PROCESS ENGINEERING, 2024, 59
[36]   Experimental and Computational Studies of the Neutral and Reduced States of Indeno[1,2-b]fluorene [J].
Rose, Bradley D. ;
Sumner, Natalie J. ;
Filatov, Alexander S. ;
Peters, Steven J. ;
Zakharov, Lev N. ;
Petrukhina, Marina A. ;
Haley, Michael M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (25) :9181-9189
[37]   3-arylthioimidazo[1,2-a]pyridine derivatives: A theoretical and experimental study of its photophysical properties [J].
Cocca, Leandro H. Zucolotto ;
Pelosi, Andre G. ;
Valverde, Joao V. P. ;
le Bescont, Julie ;
Breton-Patient, Chloe ;
Piguel, Sandrine ;
Mendonca, Cleber R. ;
De Boni, Leonardo .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2023, 440
[38]   Enantioselective Michael addition of aldehydes to maleimides organocatalysed by chiral 1,2-diamines: an experimental and theoretical study [J].
Avila, Angel ;
Chinchilla, Rafael ;
Gomez-Bengoa, Enrique ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2013, 24 (23) :1531-1535
[39]   Effect of the substituents of new coumarin-imidazo[1,2-a]heterocyclic-3-acrylate derivatives on nonlinear optical properties: a combined experimental-theoretical approach [J].
Luis Vazquez, Juan ;
Velazco-Cabral, Ivan ;
Alvarado-Mendez, Edgar ;
Trejo-Duran, Monica ;
Flores-Alamo, Marcos ;
Pena-Cabrera, Eduardo ;
Garcia-Revilla, Marco A. ;
Vazquez, Miguel A. .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (39) :22466-22475
[40]   Synthesis of novel pregnane-diosgenin prodrugs via Ring A and Ring A connection: A combined experimental and theoretical studies [J].
Sethi, Arun ;
Singh, Ranvijay Pratap ;
Shukla, Dolly ;
Singh, Praveer .
JOURNAL OF MOLECULAR STRUCTURE, 2016, 1125 :616-623