Tandem Synthesis of Photoactive Benzodifuran Moieties in the Formation of Microporous Organic Networks

Kang, Narae; Park, Ji Hoon; Ko, Kyoung Chul; Chun, Jiseul; Kim, Eun Chul; Shin, Hyun Cheol; Lee, Sang Moon; Kim, Hae Jin; Ahn, Tae Kyu; Lee, Jin Yong; Son, Seung Uk

doi:10.1002/ange.201300655

Cited by 21 publications

(7 citation statements)

References 59 publications

(27 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interestingly, in the case of H-CMP-A3, the intensity of the internal alkyne 13 C peak at 90 ppm decreased significantly, indicating the possible dangling amine addition to internal alkynes. 37,38 According to powder X-ray diffraction studies, all CMP materials in this work are noncrystalline, matching with the conventional properties of CMP materials in the literature 2 (Figure S4 in the SI).…”

Section: Acs Macro Letterssupporting

confidence: 77%

Skeleton Carbonylation of Conjugated Microporous Polymers by Osmium Catalysis for Amine-Rich Functionalization

Lee

Kim

et al. 2018

ACS Macro Lett.

Self Cite

View full text Add to dashboard Cite

This work introduces a new efficient method for the postsynthetic modification of conjugated microporous polymers (CMPs). Osmium catalysis of hollow CMP (H-CMP) in the presence of NaClO3 resulted in the conversion of alkynes in the skeleton of CMPs to dicarbonyl groups to form H-CMP-DC. Through controlling the reaction time, the carbonylation degree of H-CMP could be managed, maintaining hollow morphology. We verified the benefits of carbonyl groups in H-CMP-DC in the removal of Cr(VI) from water. Imination of H-CMP-DC resulted in amine-rich H-CMP (H-CMP-A), which showed enhanced adsorption performance toward Cr(VI) in water with q max up to 73 mg/g, compared with the H-CMP and H-CMP-DC. The H-CMP-A could be recycled at least five times, maintaining its original adsorption ability.

show abstract

Section: Acs Macro Letterssupporting

confidence: 77%

Skeleton Carbonylation of Conjugated Microporous Polymers by Osmium Catalysis for Amine-Rich Functionalization

Lee

Kim

et al. 2018

ACS Macro Lett.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Prior to the tests, CPOPs were subjected to a solution of N,N,N′,N′-tetramethyl-p-phenylenediamine (TMPD) under aerobic and irradiation conditions to verify the ability to mediate an electron-transfer process. 61,62 The color change of the solution from colorless to blue and new absorption bands at 564 and 613 nm clearly indicate the generation of the cationic radical of TMPD, which in turn proves that CPOPs have mediated the electron transfer from TMPD to dioxygen (Figure 5). The more intense absorption band for the solution containing CPOP-29 suggests stronger electron mediation ability.…”

Section: •−mentioning

confidence: 86%

Cationic Polycarbazole Networks as Visible-Light Heterogeneous Photocatalysts for Oxidative Organic Transformations

2018

View full text Add to dashboard Cite

Photoredox catalysis has aroused great interest from chemists, as it offers a powerful tool for organic synthesis. Cationic polycarbazole networks (CPOP-28 and CPOP-29) were prepared via simple oxidative coupling reaction and applied as heterogeneous photocatalysts for a wide range of oxidative organic transformations, including oxidation of sulfides, hydroxylation of arylboronic acids, and crossdehydrogenative coupling reactions, in the presence of visible light and air. Remarkably, photocatalytic activities are enhanced by ingenious introduction of trifluoromethyl groups to the polymeric network CPOP-29. The effects of the trifluoromethyl group on photocatalytic activities were elucidated in terms of photophysical and electrochemical properties. The appealing photocatalytic performance of the trifluoromethylated polymer is ascribed to superior light-absorption ability, longer fluorescence lifetime, and stronger oxidative capability. In addition, the photocatalysts showed good recyclability and could be reused after a simple separation workup.

show abstract

“…Porous organic polymers (POPs) have aroused great interest of the scientific community because of their energy storage capacities, catalytic abilities, gas sorption performances, and other applications. 1−5 Specifically, POPs have been studied as heterogeneous photocatalysts in selective oxidation of organic sulfides, 6 photocatalytic oxidative coupling of amines, 7,8 carbon−carbon bond formation, 9−12 light-induced hydrogen evolution, 13,14 or dehalogenation of α-bromoacetophenones. 15 Among POPs, conjugated porous polymers (CPPs) comprise extended π-conjugation, high chemical and thermal stability, versatile photophysical and electronic properties, and important advantages for light harvesting and heterogeneous photocatalytic applications.…”

Section: Introductionmentioning

confidence: 99%

Fluorine-Phenanthroimidazole Porous Organic Polymer: Efficient Microwave Synthesis and Photocatalytic Activity

Monterde

Navarro²,

Iglesias

et al. 2018

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

A porous polymer containing a fluorophenylphenanthroimidazole core was easily prepared via one-pot Suzuki–Miyaura cross-coupling reactions under microwave heating. These new metal-free polymers have demonstrated heterogeneous photocatalytic activity toward aza-Henry reaction with reasonable recyclability. Their preparation require a minimal workup to build porous networks with control over the apparent surface area and pore volume from suitable molecular building blocks containing 2-(1H-phenanthro[9,10-d]imidazol-2-yl)-3,5-difluorophenol (PhIm-2F), as rigid and multitopic node, which afforded a conjugated porous polymer (CPP-PhIm-2F). A series of fluorinated ligands have shown their capability in the preparation of soluble and supported cationic Ru(bpy)2(F-phenanthroimidazole) complexes by reaction with Ru(bpy)2Cl2 and demonstrating a beneficial effect of two fluorine atoms on the photocatalytic effect.

show abstract

Tandem Synthesis of Photoactive Benzodifuran Moieties in the Formation of Microporous Organic Networks

Cited by 21 publications

References 59 publications

Skeleton Carbonylation of Conjugated Microporous Polymers by Osmium Catalysis for Amine-Rich Functionalization

Skeleton Carbonylation of Conjugated Microporous Polymers by Osmium Catalysis for Amine-Rich Functionalization

Cationic Polycarbazole Networks as Visible-Light Heterogeneous Photocatalysts for Oxidative Organic Transformations

Fluorine-Phenanthroimidazole Porous Organic Polymer: Efficient Microwave Synthesis and Photocatalytic Activity

Contact Info

Product

Resources

About