1965
DOI: 10.1021/ic50033a025
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The Preparation and Properties of Some Tetracoordinate Boron Compounds. The Pseudo-Metal Ion Concept

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Cited by 61 publications
(18 citation statements)
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“…Their optical [1][2][3][4][5][6][7][8][9][10][11] and electrochemical [11][12][13][14][15][16] properties have been described in previous studies and it has been shown that they can be used as versatile uorophores, 1-5 electron acceptors 17,18 in one-electron transfer processes 19 or in chargetransport materials in both organic eld effect transistors and organic light emitting diodes. [20][21][22][23][24][25] One-electron reduction proceeds via the formation of a radical anion where the unpaired electron is delocalized on the p-system of the boroncontaining six-membered chelate ring, as demonstrated by electron paramagnetic resonance studies.…”
Section: Introductionmentioning
confidence: 99%
“…Their optical [1][2][3][4][5][6][7][8][9][10][11] and electrochemical [11][12][13][14][15][16] properties have been described in previous studies and it has been shown that they can be used as versatile uorophores, 1-5 electron acceptors 17,18 in one-electron transfer processes 19 or in chargetransport materials in both organic eld effect transistors and organic light emitting diodes. [20][21][22][23][24][25] One-electron reduction proceeds via the formation of a radical anion where the unpaired electron is delocalized on the p-system of the boroncontaining six-membered chelate ring, as demonstrated by electron paramagnetic resonance studies.…”
Section: Introductionmentioning
confidence: 99%
“…Colorless crvstals of the triclinic form were isolated directly boron, 1, and (tropolonato)diphenylboron~ 2, are stabilized by both intramolecular 0 + B interactions and by electron delocalization in the chelate rings. The chemical and physical properties of these compounds are well documented (12)(13)(14)(15)(16)(17) and references therein).…”
Section: Introductionmentioning
confidence: 99%
“…The dimerization of 1 was later recognized as a consequence of cyclic stabilization by 0-H.-N hydrogen bonding in associates like 2 (2). Six-membered dimers of the general formula 2 were also found in the solid state by X-ray crystallographic analyses of various oximes (3) and were further characterized (4) by ab initio calculations of the most simple example, formaldoxime (2, R1 = R2 = H), along with a neutron diffraction study of glyoxime at 9 K. It is known that iminoxyboranes 3, which can be envisaged as borinic acid esters of oximes, are able to dimerize in an equilibrium reaction to the six-membered BONBON ring compounds 4 if steric and electronic conditions allow the formation of a twofold Lewis acid-base adduct (5)(6)(7)(8)(9).2 Formally, in the cyclic dimer 4 both of the "chelated" protons in 2 are replaced by borenium ions (R2B+), in accordance with the concept of the chelation of "pseudometal" cations (10). In the solid state, the complete association of 3 should allow a structural characterization of the l~revious paper in this series: ref.…”
Section: Introductionmentioning
confidence: 87%