Jüngste Fortschritte in der Azaborin‐Chemie

Campbell, Patrick G.; Marwitz, Adam J. V.; Liu, Shih‐Yuan

doi:10.1002/ange.201200063

Cited by 217 publications

(12 citation statements)

References 101 publications

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“…To estimate the effect of this on the aromatic stabilization of the C 5 Br ing in 1-boraphenalenes relative to isoelectronic carbocations the isomerization method was used (calculations at the B3LYP/6-311G(d,p) level, Eq. While it has been demonstrated numerous times that the LUMOs of Bd oped PA Hs and carbocation analogues are often similar in nature, [6] to fully understand the properties of these isoelectronic pairs consideration of the occupied p orbitals is also essential. [18] This revealed that this 1-boraphenalene has am uch lower aromatic stabilization energy than the isoelectronic carbocation congener.T he lower aromatic stabilization energy for the 1-boraphenalenes was supported by an isodesmic reaction (Eq.…”

Section: Angewandte Chemiementioning

confidence: 99%

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Synthesis, Characterization, and Functionalization of 1‐Boraphenalenes

et al. 2018

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1-Boraphenalenes have been synthesized by reaction of BBr 3 with 1-(aryl-ethynyl)naphthalenes,1 -ethynylnaphthalene,a nd 1-(pent-1-yn-1-yl)naphthalene and they can be selectively functionalizeda tb oron or carbon to form benchstable products.A ll of these 1-boraphenalenes have LUMOs localized on the planar C 12 Bcore that are closely comparable in character to isoelectronic phenalenyl cations.I nc ontrast to the comparable LUMOs,the aromatic stabilization of the C 5 B ring in 1-boraphenalenes is dramatically lower than the C 6 rings in phenalenyl cations.This is due to the occupied orbitals of p symmetry being less delocalised in the 1-boraphenalenes.

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Section: Angewandte Chemiementioning

confidence: 99%

“…[6,13] In this area the combination of alkyne borylative cyclisation [14] and intramolecular boron-Friedel Crafts enabled the formation of boracycles (Scheme 1, top). [6,13] In this area the combination of alkyne borylative cyclisation [14] and intramolecular boron-Friedel Crafts enabled the formation of boracycles (Scheme 1, top).…”

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confidence: 99%

Synthesis, Characterization, and Functionalization of 1‐Boraphenalenes

et al. 2018

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“…[7] Advances in the synthetic work on azaborinine derivatives up to 2012 have been reviewed by Liu and co-workers. [8] Until recently, only very few examples of 1,4-azaborinines have been reported, all of which possessed benzo-fused polycyclic structures. [9] Very recently, Braunschweig et al reported the first successful synthesis of a monocyclic 1,4-azaborinine derivative, namely, 1,4-ditert-butyl-1,4-azaborinine (Scheme 1), by using a rhodiumcatalyzed tandem [2+2]/[2+4] cycloaddition process.…”

Section: Introductionmentioning

confidence: 99%

Photoionization and Pyrolysis of a 1,4‐Azaborinine: Retro‐Hydroboration in the Cation and Identification of Novel Organoboron Ring Systems

Holzmeier¹,

Lang²,

Hemberger³

et al. 2014

Chemistry A European J

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The photoionization and dissociative photoionization of 1,4-di-tert-butyl-1,4-azaborinine by means of synchrotron radiation and threshold photoelectron photoion coincidence spectroscopy is reported. The ionization energy of the compound was determined to be 7.89 eV. Several low-lying electronically excited states in the cation were identified. The various pathways for dissociative photoionization were modeled by statistical theory, and appearance energies AE0K were obtained. The loss of isobutene in a retro-hydroboration reaction is the dominant pathway, which proceeds with a reverse barrier. Pyrolysis of the parent compound in a chemical reactor leads to the generation of several yet unobserved boron compounds. The ionization energies of the C4 H6 BN isomers 1,2- and 1,4-dihydro-1,4-azaborinine and the C3 H6 BN isomer 1,2-dihydro-1,3-azaborole were determined from threshold photoelectron spectra.

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“…[18][19][20] Accordingly, variouso rganoboron p-conjugated molecules and polymers have been developed for organico ptoelectronic materials andd evices. [21][22][23][24][25] The boron-nitrogen coordination bond (B ! N) is one typical kind of Lewisa cid/base pair.…”

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confidence: 99%

Effects of the Substituents of Boron Atoms on Conjugated Polymers Containing B←N Units

Wang

Dou

et al. 2018

Chemistry A European J

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Organoboron chemistry is a new tool to tune the electronic structures and properties of conjugated polymers, which are important for applications in organic optoelectronic devices. To investigate the effects of substituents of boron atoms on conjugated polymers, we synthesized three conjugated polymers based on double B←N-bridged bipyridine (BNBP) with various substituents on the boron atoms. By changing the substituents from four phenyl groups and two phenyl groups/two fluorine atoms to four fluorine atoms, the BNBP-based polymers show blue-shifted absorption spectra, decreased LUMO/HOMO energy levels, and enhanced electron affinities, as well as increased electron mobilities. Moreover, these BNBP-based polymers can be used as electron acceptors for all-polymer solar cells. These results demonstrate that substituents of boron atoms can effectively modulate the electronic properties and applications of conjugated polymers.

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Jüngste Fortschritte in der Azaborin‐Chemie

Cited by 217 publications

References 101 publications

Synthesis, Characterization, and Functionalization of 1‐Boraphenalenes

Synthesis, Characterization, and Functionalization of 1‐Boraphenalenes

Photoionization and Pyrolysis of a 1,4‐Azaborinine: Retro‐Hydroboration in the Cation and Identification of Novel Organoboron Ring Systems

Effects of the Substituents of Boron Atoms on Conjugated Polymers Containing B←N Units

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