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3DPAFIPN作为一种基于卤代二氰基苯的光敏剂,催化了吡喃并[2,3-d]嘧啶骨架的克级规模光合作用。

3DPAFIPN as a halogenated dicyanobenzene-based photosensitizer catalyzed gram-scale photosynthesis of pyrano[2,3-d]pyrimidine scaffolds.

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. 2023 Aug 12;13(1):13142. doi: 10.1038/s41598-023-40360-w.

Abstract

Utilizing the Knoevenagel-Michael tandem cyclocondensation reaction of barbituric acid/1,3-dimethylbarbituric acid, malononitrile, and aryl aldehydes, a sustainable methodology for the photosynthesis of pyrano[2,3-d]pyrimidine scaffolds has been devised. The present study expounds on the development of a green radical synthetic approach toward this class of compounds. In this study, a novel halogenated dicyanobenzene-based photosensitizer was utilized in an aqueous solution, exposed to air at room temperature, and activated by a blue LED as a renewable energy source for the purpose of generating energy. The primary aim of this endeavor is to employ a recently developed, easily obtainable, and affordably priced halogenated cyanoarene-based donor-acceptor (D-A). The 3DPAFIPN [2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile]} photocatalyst, as a thermally activated delayed fluorescence (TADF), is capable of inducing single electron transfer (SET) upon irradiation with visible light, thereby offering a facile and efficient approach with a high degree of effectiveness, energy efficiency, and eco-friendliness. The aforementioned phenomenon facilitates the exploration of the temporal changes that have occurred in the interactions between the surroundings and chemical constituents. The present study aimed to investigate the turnover number (TON) and turnover frequency (TOF) for pyrano[2,3-d]pyrimidine scaffolds. Additionally, it has been demonstrated that gram-scale cyclization is a viable method for utilization in industrial applications.

摘要

利用巴比妥酸/1,3 - 二甲基巴比妥酸、丙二腈和芳醛的克诺文纳格尔 - 迈克尔串联环缩合反应,设计了一种可持续的吡喃并[2,3 - d]嘧啶骨架光合成方法。本研究阐述了针对这类化合物的绿色自由基合成方法的发展。在本研究中,一种新型的基于卤代二氰基苯的光敏剂在水溶液中使用,在室温下暴露于空气中,并由蓝色发光二极管作为可再生能源进行激活以产生能量。这项工作的主要目的是采用一种最近开发的、易于获得且价格实惠的基于卤代氰基芳烃的供体 - 受体(D - A)。3DPAFIPN [2,4,6 - 三(二苯胺)-5 - 氟间苯二甲腈]光催化剂作为热激活延迟荧光(TADF),在可见光照射下能够诱导单电子转移(SET),从而提供一种简便、高效且具有高度有效性、能源效率和生态友好性的方法。上述现象有助于探索周围环境与化学成分之间相互作用中发生的时间变化。本研究旨在研究吡喃并[2,3 - d]嘧啶骨架的周转数(TON)和周转频率(TOF)。此外,已证明克级环化是一种可用于工业应用的可行方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cde5/10423215/bb1a7a337276/41598_2023_40360_Fig1_HTML.jpg

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