Recent Advances in the Synthesis and Applications of Organoborane Polymers

Jäkle, Frieder

doi:10.1007/978-3-319-13054-5_10

Cited by 64 publications

(18 citation statements)

References 162 publications

(212 reference statements)

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“…An important recent finding in this regard was that the combination of furan rings with strongly electron-withdrawing groups substantially improves their resistance to oxidative degradation by lowering the compound’s highest occupied molecular orbital (HOMO) energy and therefore enhancing its overall stability. ,− The doping of conjugated π systems with trivalent boron atoms has emerged as an effective strategy to produce novel compounds with intriguing properties and functions. − …”

Section: Introductionmentioning

confidence: 99%

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

et al. 2021

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Doping of π-conjugated polymers or molecular compounds with trivalent boron atoms has recently emerged as a viable strategy to produce new materials with intriguing properties and functions. The combination of boron with furan moieties has been only scarcely explored so far, although the resulting furan-based materials have several notable features, including favorable optoelectronic properties and improved sustainability. Herein, we investigate the doping of α-polyfurans with a varying number of boron atoms. A series of poly(oligofuran boranes) and oligofuran-bridged bisboranes have been prepared via microwave-assisted Stille-type catalytic cross-coupling protocols. In the solid-state structures of the molecular compounds, the furan and the borane moieties exhibit a strictly coplanar arrangement; the derivative with a pentafuran bridge forms a dimeric structure in the solid state. All new compounds show considerable absorption and emission features in the visible range that arise from π–π* transitions in the oligofurylborane backbone. They are highly luminescent with quantum yields between 89 and 97% for the bisboranes and up to 87% for the difuran-bridged polymer PB2F. Their emission colors can be effectively tuned in the visible range from blue to orange via the length of the oligofuran linker. Spectroelectrochemical investigations on the difuran-bridged bisborane BB2F and polymer PB2F revealed fully reversible stepwise reductions to the respective radical anion (polaron), with absorption features in the near-infrared (NIR) region, and subsequently to a dianion (dipolaron). Overall, the doping of α-oligofurans with boron leads to a decrease of the frontier orbital energies, a reduction of the electronic band gap, and the formation of very robust and oxidatively stable materials.

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Section: Introductionmentioning

confidence: 99%

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

et al. 2021

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“…Likewise, the utility and ubiquity of boron-based compounds have bolstered the development of agricultural and material sciences [14,15]. Organoborane polymers have been investigated as electrolytes for batteries, electroactive materials, and supported Lewis acid catalysts [16,17]. Metal catalysis has had a major impact on numerous research fields from energy, biomass, environmental and water purification to synthesis of otherwise challenging and even inaccessible materials and medicinal adducts [18][19][20][21][22][23][24][25][26][27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Metal-Catalyzed Alkyl–Boron (C(sp3)–C(sp2)) Suzuki-Miyaura Cross-Couplings

El‐Maiss

Dine

et al. 2020

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Boron chemistry has evolved to become one of the most diverse and applied fields in organic synthesis and catalysis. Various valuable reactions such as hydroborylations and Suzuki–Miyaura cross-couplings (SMCs) are now considered as indispensable methods in the synthetic toolbox of researchers in academia and industry. The development of novel sterically- and electronically-demanding C(sp3)–Boron reagents and their subsequent metal-catalyzed cross-couplings attracts strong attention and serves in turn to expedite the wheel of innovative applications of otherwise challenging organic adducts in different fields. This review describes the significant progress in the utilization of classical and novel C(sp3)–B reagents (9-BBN and 9-MeO-9-BBN, trifluoroboronates, alkylboranes, alkylboronic acids, MIDA, etc.) as coupling partners in challenging metal-catalyzed C(sp3)–C(sp2) cross-coupling reactions, such as B-alkyl SMCs after 2001.

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“…The nature of this equilibrium is determined by the relative LA and LB strength, which in turn depends on both steric and electronic effects, and can be shifted by changes in temperature and concentration [ 26 , 27 ]. The facile functionalization of molecular and polymeric materials with borane Lewis acid groups makes boron-containing building blocks particularly attractive [ 28 , 29 , 30 , 31 , 32 ]. For instance, the group of Severin investigated LB-functionalized boronate esters, in particular catecholboranes, in the supramolecular self-assembly of extended networks from small molecule precursors [ 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

Polysiloxane/Polystyrene Thermo-Responsive and Self-Healing Polymer Network via Lewis Acid-Lewis Base Pair Formation

et al. 2018

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The use of thermo-reversible Lewis Pair (LP) interactions in the formation of transient polymer networks is still greatly underexplored. In this work, we describe the synthesis and characterization of polydimethylsiloxane/polystyrene (PDMS/PS) blends that form dynamic Lewis acid-Lewis base adducts resulting in reversible crosslinks. Linear PS containing 10 mol % of di-2-thienylboryl pendant groups randomly distributed was obtained in a two-step one-pot functionalization reaction from silyl-functionalized PS, while ditelechelic PDMS with pyridyl groups at the chain-termini was directly obtained via thiol-ene “click” chemistry from commercially available vinyl-terminated PDMS. The resulting soft gels, formed after mixing solutions containing the PDMS and PS polymers, behave at room temperature as elastomeric solid-like materials with very high viscosity (47,300 Pa·s). We applied rheological measurements to study the thermal and time dependence of the viscoelastic moduli, and also assessed the reprocessability and self-healing behavior of the dry gel.

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Recent Advances in the Synthesis and Applications of Organoborane Polymers

Cited by 64 publications

References 162 publications

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

Recent Advances in Metal-Catalyzed Alkyl–Boron (C(sp3)–C(sp2)) Suzuki-Miyaura Cross-Couplings

Polysiloxane/Polystyrene Thermo-Responsive and Self-Healing Polymer Network via Lewis Acid-Lewis Base Pair Formation

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