Lewis acidity enhancement of triarylborane by appended phosphine oxide groups

Introduction of a phosphine oxide group into a triarylborane significantly enhances the Lewis acidity of the boron center, the extent of which increases additively with the number of phosphine oxide groups.

Multifunctional iridium dendrimers containing peripheral carbazole/arylamine unit and/or phosphine oxide group for solution-processed electrophosphorescence

Synthetic Metals ◽

10.1016/j.synthmet.2020.116665 ◽

2021 ◽

Vol 272 ◽

pp. 116665

Author(s):

Wanyun Zhang ◽

Yi Zhang ◽

Ling Lu ◽

Siyu Zhao ◽

Xinwen Zhang ◽

...

Keyword(s):

Phosphine Oxide ◽

Solution Processed ◽

Unique reactivity of B in B[Ge9Y3]3 (Y = H, CH3, BO, CN): formation of a Lewis base

Physical Chemistry Chemical Physics ◽

10.1039/c9cp04361f ◽

2019 ◽

Vol 21 (42) ◽

pp. 23301-23304

Author(s):

G. Naaresh Reddy ◽

Rakesh Parida ◽

R. Inostroza-Rivera ◽

Arindam Chakraborty ◽

Puru Jena ◽

...

Keyword(s):

Lewis Acid ◽

Lewis Base ◽

Lewis Acidity ◽

Boron Compounds ◽

Zintl Ion ◽

Acid Nature ◽

Boron compounds usually exhibit Lewis acidity at the boron center due to the presence of vacant p-orbitals. But using Zintl-ion based groups (Ge9Y3, Y = H, CH3, BO, CN), we can alter Lewis acid nature of B to a Lewis base.

Electrophilic Substitution at Saturated Carbon. XVI. Stereochemistry of Carbanions Stabilized by Phosphine Oxide Group

Journal of the American Chemical Society ◽

10.1021/ja00891a014 ◽

1963 ◽

Vol 85 (8) ◽

pp. 1093-1096 ◽

Cited By ~ 4

Author(s):

Donald J. Cram ◽

Richard D. Partos

Keyword(s):

Phosphine Oxide ◽

Electrophilic Substitution ◽

ChemInform Abstract: Linear Coordinative Bonding at Oxygen: A Spectroscopic and Structural Study of Phosphine Oxide-Group 13 Lewis Acid Adducts.

ChemInform ◽

10.1002/chin.199033047 ◽

1990 ◽

Vol 21 (33) ◽

Author(s):

N. BURFORD ◽

B. W. ROYAN ◽

R. E. VON H. SPENCE ◽

T. S. CAMERON ◽

A. LINDEN ◽

...

Keyword(s):

Structural Study ◽

Lewis Acid ◽

Phosphine Oxide ◽

Group 13 ◽

Lewis Acid Adducts ◽

Some Dicarboxylic Acids and Esters Containing the Phosphine Oxide Group

Journal of the American Chemical Society ◽

10.1021/ja01138a017 ◽

1952 ◽

Vol 74 (18) ◽

pp. 4526-4529 ◽

Cited By ~ 46

Author(s):

Paul W. Morgan ◽

Barbara C. Herr

Keyword(s):

Phosphine Oxide ◽

Dicarboxylic Acids ◽

Differential Sensing of Saccharides Based on an Array of Fluorinated Benzosiloxaborole Receptors

Sensors ◽

10.3390/s20123540 ◽

2020 ◽

Vol 20 (12) ◽

pp. 3540

Author(s):

Paweł Ćwik ◽

Patrycja Ciosek-Skibińska ◽

Marcin Zabadaj ◽

Sergiusz Luliński ◽

Krzysztof Durka ◽

...

Keyword(s):

Binding Sites ◽

Clustering Analysis ◽

Lewis Acidity ◽

Alizarin Red ◽

Molecular Receptors ◽

Potential Binding ◽

Receptor Array ◽

Ph Conditions ◽

Shed Light ◽

Fluorinated benzosiloxaboroles–silicon congeners of benzoxaboroles, were synthesized and tested as molecular receptors for mono- and disaccharides. The receptors differed in the Lewis acidity of the boron center as well as in the number of potential binding sites. The calculated stability constants indicated different binding affinity of benzosiloxaborole derivatives towards selected saccharides, enabling their classification using a receptor array-based sensing. Unique fluorescence fingerprints were created on the basis of competitive interactions of the studied receptors with both Alizarin Red S (ARS) and tested saccharide molecules. Detailed chemometric analysis of the obtained fluorescence data (based on partial least squares-discriminant analysis and hierarchical clustering analysis) provided the differential sensing of common saccharides, in particular the differentiation between glucose and fructose. In addition, DFT calculations were carried out to shed light on the binding mechanism under different pH conditions.

Synthesis and structure of new 2-aryl-substituted pyrrolidines containing phosphine oxide group

Mendeleev Communications ◽

10.1016/j.mencom.2018.07.019 ◽

2018 ◽

Vol 28 (4) ◽

pp. 398-400 ◽

Cited By ~ 3

Author(s):

Liliya I. Vagapova ◽

Julia K. Voronina ◽

Victor V. Syakaev ◽

Alexander R. Burilov ◽

Airat R. Garifzyanov ◽

...

Keyword(s):

Phosphine Oxide ◽

Intrinsically heat-sealable polyimide films with atomic oxygen resistance: Synthesis and characterization

High Performance Polymers ◽

10.1177/0954008320908652 ◽

2020 ◽

Vol 32 (8) ◽

pp. 902-913 ◽

Cited By ~ 1

Author(s):

Hongjiang Ni ◽

Yu Xing ◽

Xiaoxiang Dai ◽

Daijun Zhang ◽

Jun Li ◽

...

Keyword(s):

Molecular Structure ◽

Mechanical Property ◽

Thermal Resistance ◽

Mechanical Strength ◽

Phosphine Oxide ◽

Atomic Oxygen ◽

Synthesis And Characterization ◽

Polyimide Films ◽

Diphenylphosphine Oxide ◽

Intrinsically heat-sealable polyimides with atomic oxygen (AO) resistance (ARPIs) were synthesized from 2,3,3′,4′-oxydiphthalic anhydride (aODPA), 2,5-bis[(4-aminophenoxy)phenyl]diphenylphosphine oxide (BADPO), and para-phenylenediamine (PDA). The effects of the molecular structure and diamine ratio were investigated on the properties of the ARPI, including mechanical property, thermal property, heat sealability, and AO resistance. Heat sealability and AO resistance were realized for the ARPI film by combining the asymmetry of the aODPA moiety and the passivated layer forming characteristic of diphenylphosphine phosphine oxide group. Meanwhile, the deficiency of low mechanical strength and thermal resistance, commonly existing in a completely BADPO-derived polyimide system, was remedied effectively by the higher reactivity and rigidity of PDA.

Ketone coordination chemistry of the diborane t-BuCH=C[B(C6F5)2]2

Canadian Journal of Chemistry ◽

10.1139/v98-170 ◽

1998 ◽

Vol 76 (9) ◽

pp. 1249-1255 ◽

Cited By ~ 11

Author(s):

Katrin Köhler ◽

Warren E Piers

Keyword(s):

Coordination Chemistry ◽

Nmr Spectroscopy ◽

Low Temperature ◽

Temperature Dependence ◽

Key Words ◽

Lewis Acidity ◽

High Yield ◽

Lewis Bases ◽

Equilibrium Yield ◽

Reactions of the bifunctional borane t-BuCH=C[B(C6F5)2]2, 1, with simple Lewis bases were investigated to probe its Lewis acidity. Ethereal bases (Et2O, THF) bind very weakly, if at all, as no adducts were detectable in solution. Certain ketones, however, were observed to bind to 1. Acetone forms an adduct, 2, reversibly in solution (Keq at 293 K = 69.1), and the temperature dependence of this equilibrium yield thermodynamic parameters of H° = -59.5 ± 2.0 kJ mol-1; S° = -167 ± 4 J K-1 mol-1. Low temperature NMR spectroscopy suggests that the acetone binds to the more sterically accessible boron center trans to the t-Bu group. Ketone binding is strengthened when 2,3-diphenylcyclopropenone is reacted with 1, irreversibly forming an isolable adduct, 4, in high yield (95%). The availability of a resonance form incorporating the aromatic cyclopropenyl cation contributes to the added stability of this adduct in comparison to 2.Key words: organoboranes, diboranes, ketone complexes.