Zirconium based porous coordination polymer (PCP) bearing organocatalytic ligand: A promising dual catalytic center for ultrasonic heterocycle synthesis

Paria Panahi; Nasrin Nouruzi; Esmail Doustkhah; Hamed Mohtasham; Arefeh Ahadi; Azra Ghiasi-Moaser; Sadegh Rostamnia; Ghodrat Mahmoudi; Alireza Khataee

doi:10.1016/j.ultsonch.2019.104653

Zirconium based porous coordination polymer (PCP) bearing organocatalytic ligand: A promising dual catalytic center for ultrasonic heterocycle synthesis

Ultrason Sonochem. 2019 Nov:58:104653. doi: 10.1016/j.ultsonch.2019.104653. Epub 2019 Jun 21.

Authors

Paria Panahi¹, Nasrin Nouruzi¹, Esmail Doustkhah², Hamed Mohtasham¹, Arefeh Ahadi¹, Azra Ghiasi-Moaser¹, Sadegh Rostamnia³, Ghodrat Mahmoudi⁴, Alireza Khataee⁵

Affiliations

¹ Organic and Nano Group (ONG), Department of Chemistry, Faculty of Science, University of Maragheh, PO Box 55181-83111, Maragheh, Iran.
² Organic and Nano Group (ONG), Department of Chemistry, Faculty of Science, University of Maragheh, PO Box 55181-83111, Maragheh, Iran; International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan.
³ Organic and Nano Group (ONG), Department of Chemistry, Faculty of Science, University of Maragheh, PO Box 55181-83111, Maragheh, Iran. Electronic address: rostamnia@maragheh.ac.ir.
⁴ Department of Chemistry, Faculty of Science, University of Maragheh, PO Box 55181-83111, Maragheh, Iran. Electronic address: mahmoudi_ghodrat@yahoo.co.uk.
⁵ Research Laboratory of Advanced Water and Wastewater Treatment Processes, Department of Applied Chemistry, Faculty of Chemistry, University of Tabriz, 51666-16471 Tabriz, Iran; Department of Materials Science and Nanotechnology Engineering, Faculty of Engineering, Near East University, 99138 Nicosia, Mersin 10, Turkey. Electronic address: a_khataee@tabrizu.ac.ir.

PMID: 31450335
DOI: 10.1016/j.ultsonch.2019.104653

Abstract

Herein, the efficient role of ultrasonic irradiation both in synthesis of Zr based porous coordination polymer (Zr-PCP) nanoparticles and boosting its catalytic activity, towards the benzimidazoles synthesis is represented. We use an amine based ligand (amino-terephthalate) for PCP and we exhibit that it can have a synergistic catalytic activity. In this work, a unique nano-engineering of cooperative and synergistic catalytic activity of zirconium, as a Lewis acid, and aminophenylene, as an organocatalyst, in the synthesis of heterocycles is presented for the synthesis of benzimidazole from cascade reaction of phenylene diamine with aldehyde at ambient temperature. Zr and amine groups of the Zr-PCP are active catalytic sites which in combination with the ultrasonic irradiation leads to a high selectivity and rapid catalytic production of benzylimidazoles. N₂ adsorption-desorption along with BJH analyses confirm the microporosity of the catalyst and recyclability shows that the catalyst is green and sustainable heterogeneous microporous catalyst.

Keywords: Benzimidazole; Green catalyst; Sonochemical synthesis; Ultrasound irradiation; Zr-PCP-NH(2).