N-Coordinated Organoboron in Polymer Synthesis and Material Science

He, Congze; Dong, Jin; Xu, Chaoran; Pan, Xiangcheng

doi:10.1021/acspolymersau.2c00046

Cited by 12 publications

(11 citation statements)

References 147 publications

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“…34 Donor−acceptor type B ← N coordinate bonds are unique as they are generally energetically stronger than traditional noncovalent interactions (e.g., hydrogen/halogen bonding and stacking interactions), directional, and reversible in nature. 29,35,36 Although N-coordinated organoboron chemistry has already been widely exploited for routine solution-mediated supramolecular polymer synthesis, 29,34,37 visible light-induced topochemical preparation of single-crystalline organoboron polymers has never been reported so far. In fact, topochemical construction of singlecrystalline B ← N polymers can provide a new toolbox to chemists for the synthesis of ordered functional supramolecular polymers, 38 having unique structural topologies and properties within the realm of organoboron chemistry.…”

Section: ■ Introductionmentioning

confidence: 99%

Single-Crystal-to-Single-Crystal Photosynthesis of Supramolecular Organoboron Polymers with Dynamic Effects

Bhandary,

Beliš,

Shukla

et al. 2024

J. Am. Chem. Soc.

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The solid-state synthesis of single-crystalline organic polymers, having functional properties, remains an attractive and developing research area in polymer chemistry and materials science. However, light-triggered topochemical synthesis of crystalline polymers comprising an organoboron backbone has not yet been reported. Here, we describe an intriguing example of single-crystal-tosingle-crystal (SCSC) rapid photosynthesis (occurs on a secondsscale) of two structurally different linear organoboron polymers, driven by environmentally sustainable visible/sun light, obtained from the same monomer molecule. A newly designed Lewis acid−base type molecular B ← N organoboron adduct (consisting of an organoboron core and naphthylvinylpyridine ligands) crystallizes in two solid-state forms featuring the same chemical structure but different 3D structural topologies, namely, monomers 1 and 2. The solvate molecule-free crystals of 1 undergo topochemical photopolymerization via an unusual olefin−naphthyl ring [2 + 2] cyclization to yield the single crystalline [3]-ladderane polymer 1P growing along the B ← N linkages, accompanied by instantaneous and violent macroscopic mechanical motions or photosalient effects (such as bendingreshaping and jumping motions). In contrast, visible light-harvesting single crystals of 2 quantitatively polymerize to a B ← N bondstabilized polymer 2P in a SCSC fashion owing to the rapid [2 + 2] cycloaddition reaction among olefin double bonds. Such olefin bonds in the crystals of 2 are suitably preorganized for photoreaction due to the presence of solvate molecules in the crystal packing. Single crystals of 2 also show photodynamic jumping motions -in response to visible light but in a relatively slower fashion than the crystals of 1. In addition to SCSC topochemical polymerization and dynamic motions, both monomer crystals and their singlecrystalline polymers feature green emissive and short-lived room-temperature phosphorescence properties upon excitation with visible-light wavelength.

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Section: ■ Introductionmentioning

confidence: 99%

Single-Crystal-to-Single-Crystal Photosynthesis of Supramolecular Organoboron Polymers with Dynamic Effects

Bhandary,

Beliš,

Shukla

et al. 2024

J. Am. Chem. Soc.

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“…Materials that are assembled using, for example, N,O-or N,C-chelate ligands are not discussed but are included in some recent reviews to which the interested reader is referred to. [18] We will also not elaborate on aminoborane polymers with alternating B and N atoms in the main chain, which may be considered as polymeric forms of iminoboranes that are assembled through BÀ N LP bonding. The reader is referred to an excellent review by Manners and co-workers on this topic.…”

Section: Introductionmentioning

confidence: 99%

Boron‐Nitrogen Lewis Pairs in the Assembly of Supramolecular Macrocycles, Molecular Cages, Polymers, and 3D Materials

Chen,

Jäkle

2023

Angew Chem Int Ed

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Covering an exceptionally wide range of bond strengths, the dynamic nature and facile tunability of dative B−N bonds is highly attractive when it comes to the assembly of supramolecular polymers and materials. This Minireview offers an overview of advances in the development of functional materials where Lewis pairs (LPs) play a key role in their assembly and critically influence their properties. Specifically, we describe the reversible assembly of linear polymers with interesting optical, electronic and catalytic properties, discrete macrocycles and molecular cages that take up diverse guest molecules and undergo structural changes triggered by external stimuli, covalent organic frameworks (COFs) with intriguing interlocked structures that can embed and separate gases such as CO2 and acetylene, and soft polymer networks that serve as recyclable, self‐healing, and responsive thermosets, gels and elastomeric materials.

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“…Organoboron is a class of compounds have a broad range of applications in materials science such as dynamic covalent materials, [1][2][3][4] optical and electrochemical sensors, [5][6][7] nanomaterials, [8][9][10][11][12] functionalized biomaterials, [13][14][15][16] natural products, [17][18][19] agrochemicals, [20][21] and pharmaceuticals chemistry as the active drugs molecules [22][23][24][25][26][27][28][29] for instances Velcade, Ninlaro etc. (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Progress in the Electrochemical Synthesis of Organoboron Compounds

Moniruzzaman

Afrin

Ali³

2023

Asian J Org Chem

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Organoboron is a class of compounds widely used in organic synthesis, pharmaceuticals, material science, sensors, and so on. Therefore, the development of efficient and selective electrochemical methods to synthesize organoboron has attracted much interest as an emerging sustainable technique of organic synthesis. Here, we summarized research on electrochemical borylations, including the electrochemically driven borylation of arenes, alkanes, aryl, or alkyl halides, activated carboxylic acids etc., based on direct electrolysis and metal‐free organocatalysis. We focus on the reaction mechanisms involved in single‐electron transfer and other radical processes. We believe that this review will inspire electrochemists to discover more efficient transformations to expand this field of borylation.

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N-Coordinated Organoboron in Polymer Synthesis and Material Science

Cited by 12 publications

References 147 publications

Single-Crystal-to-Single-Crystal Photosynthesis of Supramolecular Organoboron Polymers with Dynamic Effects

Single-Crystal-to-Single-Crystal Photosynthesis of Supramolecular Organoboron Polymers with Dynamic Effects

Boron‐Nitrogen Lewis Pairs in the Assembly of Supramolecular Macrocycles, Molecular Cages, Polymers, and 3D Materials

Progress in the Electrochemical Synthesis of Organoboron Compounds

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