A diiodo-BODIPY postmodified metal–organic framework for efficient heterogeneous organo-photocatalysis

Quan, Ying; Li, Qiuyan; Zhang, Quan; Zhang, Wenqiang; Han, Lu; Yu, Jun-Hao; Chen, Jian; Zhao, Xinsheng; Wang, Xiaojun

doi:10.1039/c6ra03516g

Cited by 27 publications

(14 citation statements)

References 57 publications

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“…Both noble transition metal and organic dye based photocatalysts have been successfully applied in various organic transformations. − However, one disadvantage for this kind of homogeneous catalyst is the difficulty in recycling for multiuse. To solve the problem, one solution is to develop a heterogeneous photocatalyst for catalytic organic systhesis, and many achievements have been made in this field. − Another option is to apply various types of support materials in immobilization of these homogeneous photocatalysts, such as polymers, − silicas, − graphene, and metal–organic frameworks (MOFs). − Using materials in daily life as support for organic catalyst’s immobilizaition is quite interesting and more practical, but it is rare. In 2013, List et al reported the application of polyamide textiles as organocatalyst support for several catalytic organic transformations, to develop so-called “Organotextile Catalysis” .…”

Section: Introductionmentioning

confidence: 99%

Organic Cotton Photocatalysis

Xiao

Huang

Luo

et al. 2018

ACS Sustainable Chem. Eng.

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Cotton fiber is an abundant natural material, which has a long history of application in human daily life. However, a report on using such material in catalysis for organic synthesis is rare. We envisaged that the hydroxyl groups on the surface of cotton fiber could be utilized for functionalization and further immobilization of organic catalysts. In this report, we demonstrate the facile functionalization of cotton fiber by growing polymer brushes on its surface and further anchoring of Rose Bengal (RB) organic photocatalyst. This novel composite cotton photocatalyst demonstrated high efficiency in catalyzing crossdehydrogenative coupling reactions and N-demethylation reactions with irradiation of visible light. The catalytic reaction can be facilely scaled up by a homemade circulating flow reactor.

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Section: Introductionmentioning

confidence: 99%

Organic Cotton Photocatalysis

Xiao

Huang

Luo

et al. 2018

ACS Sustainable Chem. Eng.

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“…A mechanism similar to the previous one was proposed to explain the formation of products 6 and 8 (See Scheme 3). A porous material‐immobilized iodo‐Bodipy dye has also been successfully employed in the oxidation/[3+2] cycloaddition/aromatization tandem reaction [29] while the groups of Li, Zhao, and Wang prepared a diiodo‐Bodipy postmodified metal‐organic framework which was applied to the aerobic reaction of N ‐aryl tetrahydroisoquinolines 1 with nitroalkanes 2 and the reaction of tetrahydroisoquinoline 4 with N ‐aryl and N ‐benzyl maleimides [30] . For both heterogeneous photocatalysts, recycling studies were carried out without a significant decrease in the yields after three reactions.…”

Section: Applications Of Bodipy In Photoorganocatalysismentioning

confidence: 99%

State of the Art of Bodipy‐Based Photocatalysts in Organic Synthesis

et al. 2021

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Photochemistry is a tremendous research field offering many synthetic possibilities to chemists. Breakthroughs in this area have been notably driven by the implementation of new classes of photocatalysts. Within this context, Bodipy (Boron-dipyrromethene) dyes possess attractive chemical and physical features such as their modularity, strong absorption under visible light irradiation, good thermal and photochemical stabilities, and high fluorescence quantum yields. As such, this class of compounds has found widespread applications in functionalized materials, biology, medicine, or organic chemistry. From an organic-synthetic point of view, excited states of Bodipy dyes have been harnessed in electron and energy transfer reactions. This minireview collates the relevant literature on the applications of these catalysts in synthetic photochemistry and provides some perspectives of this research area.

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“…In this sense, for MOFs, the covalent anchorage of different photosensitizers (Vitamin B2 [68], BODIPY [69], Eosin Y [70] or subphtalocyanine [71]) has allowed the obtaining of heterogeneous photocatalysts that generally present higher stability and photocatalytic activity than their homogeneous versions (Figure 8). This enhancement can be due to the immobilization and isolation of photocatalytically active species, hampering unproductive encounters between photoexcited intermediates and, sometimes, leading to a change on the reaction mechanism.…”

Section: Functionalized Materialsmentioning

confidence: 99%

“…The same strategy was later employed by Khan and collaborators [70], who anchored the organic photocatalyst The functionalization strategy has also been applied in obtaining MOFs with photocatalytic activity for CDC reactions. Thus, a BODIPY photosensitizer was anchored to UiO-68 through pending amino groups present in the linkers [69]. The UiO-68-BP was employed as heterogeneous photocatalyst for CDC reactions among different N-aryl-THIQs and different nitroalkanes.…”

Section: Cross-dehydrogenative Couplingmentioning

confidence: 99%

Metal–Organic Frameworks (MOFs) and Covalent Organic Frameworks (COFs) Applied to Photocatalytic Organic Transformations

et al. 2020

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Among the different alternatives for catalysis using metal–organic frameworks (MOFs) or covalent organic frameworks (COFs), photocatalysis has remarkably evolved during the last decade. Photocatalytic reticular materials allowed recyclability and easy separation of catalyst from the product, also reaching the activity and selectivity commonly observed for molecular systems. Recently, photocatalytic MOFs and COFs have been applied to synthetic applications in order to obtain organic molecules of different complexity. However, although a good number of works have been devoted to this issue, an updated comprehensive revision on this field is still needed. The aim of this review was to fill this gap covering the following three general aspects: (1) common strategies on the design of reticular photocatalytic materials, (2) a comprehensive discussion of the photocatalytic organic reactions achieved by the use of COFs and MOFs, and (3) some critical considerations highlighting directions that should be considered in order to make advances in the study of photocatalytic COFs and MOFs.

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A diiodo-BODIPY postmodified metal–organic framework for efficient heterogeneous organo-photocatalysis

Abstract: A diiodo-BODIPY postmodified MOF acts as a highly active and recyclable heterogeneous photocatalyst for aerobic CDC and oxidation/[3 + 2]cycloaddition reactions under visible light irradiation.

Cited by 27 publications

References 57 publications

Organic Cotton Photocatalysis

Organic Cotton Photocatalysis

State of the Art of Bodipy‐Based Photocatalysts in Organic Synthesis

Metal–Organic Frameworks (MOFs) and Covalent Organic Frameworks (COFs) Applied to Photocatalytic Organic Transformations

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