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以新型供体-受体荧光团1,2,3,5-四(咔唑-9-基)-4,6-二氰基苯(4CzIPN)催化合成多官能化二氢-2-氧代吡咯。

Synthesis of polyfunctionalized dihydro-2-oxypyrroles catalyzed by 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a novel donor-acceptor fluorophore.

作者信息

Mohamadpour Farzaneh

机构信息

School of Engineering, Apadana Institute of Higher Education, Shiraz, Iran.

出版信息

Sci Rep. 2022 Oct 7;12(1):16911. doi: 10.1038/s41598-022-20689-4.

DOI:10.1038/s41598-022-20689-4
PMID:36207337
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9547064/
Abstract

We developed a green radical synthesis method for polyfunctionalized dihydro-2-oxypyrroles based on the Michael-Mannich cyclocondensation of amines, dialkyl acetylenedicarboxylates, and formaldehyde. To generate a renewable energy sources from visible light, a PCET (proton-coupled electron transfer) photocatalyst was used in an ethanol solution in an air environment and at room temperature. In this study, we aim to develop an inexpensive and easily accessible novel donor-acceptor (D-A) fluorophore. Besides its speed-saving features and ease of use, the carbazole-based photocatalyst (4CzIPN) also shows high yields, energy-efficient, and is environmentally friendly. In this way, it is possible to monitor changes in chemical and environmental variables over time. The variety of yields is pretty uniform (84-97%, average 92.3%), and the kind of response times be very speedy (15-25 min, average 17.6 min), and the element noted within the dialogue is that the system tolerates a variety of donating and withdrawing functional groups, at the same time as nevertheless giving very fast rate and tremendous yields. A study of polyfunctionalized dihydro-2-oxypyrroles was conducted to calculate the turnover number (TON) and turnover frequency (TOF). Gram-scale cyclization proves that it can be applied to industry in a practical manner.

摘要

我们基于胺、二烷基乙炔二羧酸酯和甲醛的迈克尔-曼尼希环缩合反应,开发了一种用于多官能化二氢-2-氧代吡咯的绿色自由基合成方法。为了从可见光中产生可再生能源,在空气环境和室温下,在乙醇溶液中使用了质子耦合电子转移(PCET)光催化剂。在本研究中,我们旨在开发一种廉价且易于获得的新型供体-受体(D-A)荧光团。除了其节省时间的特性和易用性外,咔唑基光催化剂(4CzIPN)还具有高产率、高能效且环境友好的特点。通过这种方式,可以监测化学和环境变量随时间的变化。产率的变化相当均匀(84-97%,平均92.3%),响应时间非常迅速(15-25分钟,平均17.6分钟),并且该体系能够耐受各种供电子和吸电子官能团,同时仍能给出非常快的反应速率和高收率。对多官能化二氢-2-氧代吡咯进行了研究以计算周转数(TON)和周转频率(TOF)。克级环化反应证明它可以实际应用于工业生产。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/96652943392f/41598_2022_20689_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/398904cbc211/41598_2022_20689_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/0da618c14c44/41598_2022_20689_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/df528805735b/41598_2022_20689_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/f1a88d2efdbe/41598_2022_20689_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/da88902d2c35/41598_2022_20689_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/96652943392f/41598_2022_20689_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/398904cbc211/41598_2022_20689_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/0da618c14c44/41598_2022_20689_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/df528805735b/41598_2022_20689_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/f1a88d2efdbe/41598_2022_20689_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/da88902d2c35/41598_2022_20689_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a0ac/9547064/96652943392f/41598_2022_20689_Fig6_HTML.jpg

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