Organocatalytic orthogonal ATRP and ring-opening polymerization using a single dual-function photocatalyst

Ma, Qiang; Jiang, Yu; Lin, Junqiang; Zhang, Xun; Shao, Hui; Liao, Saihu

doi:10.1039/d2py00633b

Cited by 7 publications

(10 citation statements)

References 64 publications

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“…20 The development of novel and effective organic photocatalysts for O-ATRP has become a focus of extensive research efforts since 2014. 21 Benzophenone as a photoinitiator has been proved to activate the O-ATRP of vinyl monomers together with N , N , N ′, N ′′, N ′′-pentamethyldiethylenetriamine as an electron donor source. 22 Therefore, we examined these phenanthrenones as a photocatalyst for the O-ATRP of MMA, in which diethyl bromo(methyl)malonate (DBMM) was used as the initiator and dimethylacetamide (DMA) as the solvent.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst

Gan¹,

Zhou²,

Zhu³

et al. 2023

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst

Gan¹,

Zhou²,

Zhu³

et al. 2023

Org. Chem. Front.

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“…These compounds were used in combination with BH 3 ·THF to promote the asymmetric Diels–Alder reactions. ( R )- or ( S )- 133 were also used to prepare other BINOL-based compounds for various applications. − …”

Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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1,1′-Bi-2-naphthol (BINOL) has been extensively used as the chirality source in the fields of molecular recognition, asymmetric synthesis, and materials science. The direct electrophilic substitution at the aromatic rings of the optically active BINOL has been developed as one of the most convenient strategies to structurally modify BINOL for diverse applications. High regioselectivity has been achieved for the reaction of BINOL with electrophiles. Depending upon the reaction conditions and substitution patterns, various functional groups can be introduced to the specific positions, such as the 6-, 5-, 4-, and 3-positions, of BINOL. Ortho-lithiation at the 3-position directed by the functional groups at the 2-position of BINOL have been extensively used to prepare the 3- and 3,3′-substituted BINOLs. The use of transition metal-catalyzed C–H activation has also been explored to functionalize BINOL at the 3-, 4-, 5-, 6-, and 7-positions. These regioselective substitutions of BINOL have allowed the construction of tremendous amount of BINOL derivatives with fascinating structures and properties as reviewed in this article. Examples for the applications of the optically active BINOLs with varying substitutions in asymmetric catalysis, molecular recognition, chiral sensing and materials are also provided.

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“…It is well known that the discovery of excellent photosensitizers (PS, including photocatalysts [PC] and photoinitiators [PI]) is the most crucial link, as they allow a spatio‐temporal macroscopic control of the (co)polymerization process (molecular weight, polydispersity, curing rate, etc.) 11–16 …”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9][10] It is well known that the discovery of excellent photosensitizers (PS, including photocatalysts [PC] and photoinitiators [PI]) is the most crucial link, as they allow a spatio-temporal macroscopic control of the (co)polymerization process (molecular weight, polydispersity, curing rate, etc.). [11][12][13][14][15][16] A PI (or PC) can obviously also play the role of a PS in the sense of photochemistry. 17 The design and development of promising PIs (or PCs, organic or organometallic compounds) exhibiting excellent light absorption properties (especially in the visible light wavelength range with high molar extinction coefficients) and being able to be incorporated in systems-PI or PC + additive (s)-is highly interesting for polymer synthesis [18][19][20] and attracts increasing interests in fields varying from traditional applications (like coatings, adhesives, inkjet printings, etc.…”

Section: Introductionmentioning

confidence: 99%

Dual photo/thermal initiation with charge transfer complexes based on bromide‐based electron acceptors

Zhang

Liu

et al. 2023

Journal of Polymer Science

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Different combinations of donors and acceptors of charge transfer complexes (CTCs) can realize visible light catalysis in multiple wavelength bands. Here, we successfully demonstrated that 2‐bromoacetophenone as an electron acceptor, combined with amines (for formation of CTC), can achieve photopolymerization under LED@405 nm visible light irradiation, initiating the polymerization of (meth)acrylates, and the induction time can be completely eliminated by condition optimization. The CTC was also shown to have dual photo/thermal initiation capability and was eventually applied to 3D printing as well.

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Organocatalytic orthogonal ATRP and ring-opening polymerization using a single dual-function photocatalyst

Abstract: Orthogonal catalysis is emerging as a powerful tool for the synthesis of block copolymers. By employing a single designed dual-function photoredox phosphoric acid catalyst (Photo-PA), the two types of polymerizations...

Cited by 7 publications

References 64 publications

Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst

Synthesis, properties, and application of phenanthrenone: an undeveloped building block and a photocatalyst

Regioselective Substitution of BINOL

Dual photo/thermal initiation with charge transfer complexes based on bromide‐based electron acceptors

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