Sulfonamide-functionalized covalent organic framework (COF-SO 3 H): an efficient heterogeneous acidic catalyst for the o
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Sulfonamide‑functionalized covalent organic framework (COF‑SO3H): an efficient heterogeneous acidic catalyst for the one‑pot preparation of polyhydroquinoline and 1,4‑dihydropyridine derivatives Razieh Farsi1 · Mohammad Kazem Mohammadi1 · Seyyed Jafar Saghanezhad2 Received: 9 July 2020 / Accepted: 2 November 2020 © Springer Nature B.V. 2020
Abstract Herein, we report the sulfonamide-functionalized covalent organic framework (COF-SO3H) prepared from melamine and terephthalaldehyde and subsequent sulfonation, as an acidic porous catalyst for the one-pot preparation of polyhydroquinoline and 1,4-dihydropyridine derivatives. COF-SO3H was characterized by FT-IR, EDX, TGA, SEM, XRD, and BET. This methodology offers several advantages including high yield, short reaction time, simple workup procedure, solvent-free conditions, ease of separation, and recyclability.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04322-5) contains supplementary material, which is available to authorized users. * Mohammad Kazem Mohammadi [email protected] 1
Department of Chemistry, Islamic Azad University, Ahvaz Branch, Ahvaz, Iran
2
ACECR-Production Technology Research Institute, Ahvaz, Iran
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Graphic abstract One-pot preparation of polyhydroquinoline and 1, 4-dihydropyridinederivatives
Keywords Covalent organic framework (COF) · Nanoporous · Melamine · Terephthalaldehyde · Acidic catalyst · Chlorosulfonic acid
Introduction Over the past decade, interest in the field of nanoporous materials as regular organic or inorganic frameworks has grown tremendously because of their excellent porous properties and broad applications [1]. As an emerging kind of crystalline porous materials, covalent organic frameworks (COFs) pioneered by Yaghi and co-workers in 2005 are composed of two organic moieties via strong covalent bonds between light atoms (e.g., H, B, C, N, O, Si) to generate long-range ordered two-dimensional (2D) or three-dimensional (3D) network structures [2–5]. A wide range of porous organic polymers (POPs), which are also called porous organic materials [6], have been introduced in the past two decades, such as COFs and various amorphous networks, such as hypercrosslinked polymers (HCPs), covalent triazine frameworks (CTFs), porous aromatic frameworks (PAFs), and conjugated microporous polymers (CMPs) [7–9]. Due to their fascinating properties, such as high surface area, viscous cavities, and high porosity, low-density economical materials are obtained due to the low-cost starting materials and the easy way of synthesis. High thermal and chemical stability endows COFs with a wide application potential in the fields of energy storage, gas adsorption, drug delivery, catalysis, sensing, and optoelectronics
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Sulfonamide‑functionalized covalent organic framework…
[10–15]. Functionalization in the course of synthesis and/or post-functionalization of COFs endows their framework with specific active sites, which could furt
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