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利用闭环复分解反应、克劳森-卡斯反应、范勒森反应和乌尔曼型反应作为关键工具,设计、合成新型星形并四苯基杂环及其光物理性质

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson-Kaas, Van Leusen and Ullmann-type reactions as key tools.

作者信息

Alvi Shakeel, Ali Rashid

机构信息

Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, Okhla, New Delhi-110025, India.

出版信息

Beilstein J Org Chem. 2021 Jun 2;17:1374-1384. doi: 10.3762/bjoc.17.96. eCollection 2021.

DOI:10.3762/bjoc.17.96
PMID:34136016
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8182681/
Abstract

Design, synthesis and properties of polycyclic aromatic hydrocarbons (PAHs) has historically attracted a considerable interdisciplinary interest from both fundamental as well as applied viewpoint on account of their wonderful optoelectronic properties. The scientific interest in two-dimensional star-shaped PAHs particularly in truxene architectures arises because of their high thermal stability, exceptional solubility and ease with which they can be constructed and modified. Therefore, bearing in mind a wide range of applications of truxene and its congeners, herein we reveal three novel distinctly different routes for the generation of -symmetric pyrrole-based truxene architectures by means of cyclotrimerization, ring-closing metathesis (RCM), Clauson-Kaas and Ullmann-type coupling reactions as key steps. Moreover, we have also assembled some other interesting heterocyclic systems possessing oxazole, imidazole, benzimidazole, and benzoxazole in the framework of truxene. Additionally, the preliminary photophysical properties (absorption and emission) for these versatile systems has been revealed.

摘要

多环芳烃(PAHs)的设计、合成及性质,因其出色的光电性能,从基础和应用的角度来看,长期以来一直吸引着相当多的跨学科关注。对二维星形PAHs,特别是对特鲁克斯烯结构的科学兴趣,源于它们的高热稳定性、出色的溶解性以及易于构建和修饰的特点。因此,考虑到特鲁克斯烯及其同系物的广泛应用,在此我们揭示了三种全新且明显不同的路线,通过环三聚反应、关环复分解反应(RCM)、克劳森 - 卡斯反应和乌尔曼型偶联反应作为关键步骤来生成对称的基于吡咯的特鲁克斯烯结构。此外,我们还在特鲁克斯烯框架内组装了一些其他有趣的含有恶唑、咪唑、苯并咪唑和苯并恶唑的杂环体系。此外,还揭示了这些多功能体系的初步光物理性质(吸收和发射)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/8337df8adf71/Beilstein_J_Org_Chem-17-1374-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/ca2a7322bf63/Beilstein_J_Org_Chem-17-1374-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/ce7223877d9b/Beilstein_J_Org_Chem-17-1374-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/8520084bfd13/Beilstein_J_Org_Chem-17-1374-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/aa077cd0c154/Beilstein_J_Org_Chem-17-1374-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/aaf6b0b70c46/Beilstein_J_Org_Chem-17-1374-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/e28b45e21855/Beilstein_J_Org_Chem-17-1374-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/0f2a8336802d/Beilstein_J_Org_Chem-17-1374-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/8337df8adf71/Beilstein_J_Org_Chem-17-1374-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/ca2a7322bf63/Beilstein_J_Org_Chem-17-1374-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/ce7223877d9b/Beilstein_J_Org_Chem-17-1374-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/8520084bfd13/Beilstein_J_Org_Chem-17-1374-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/aa077cd0c154/Beilstein_J_Org_Chem-17-1374-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/aaf6b0b70c46/Beilstein_J_Org_Chem-17-1374-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/e28b45e21855/Beilstein_J_Org_Chem-17-1374-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/0f2a8336802d/Beilstein_J_Org_Chem-17-1374-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cd1/8182681/8337df8adf71/Beilstein_J_Org_Chem-17-1374-g002.jpg

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