Fluorescent Ethenyl- and Ethynyl-dimesitylboranes Derived from 5-(Dimethylamino)-N-(prop-2-ynyl)naphthalene-1-sulfonamide

Two new fluorescent ethenyl- and ethynyl-dimesitylboranes functionalized with a dansyl group 1 and 2 have been synthesized in good yields. Compound 1 was prepared by the hydroboration of 5-(dimethylamino)-N-(prop-2-ynyl)naphthalene-1-sulfonamide I with dimesitylborane (HB(Mes)2) in dry tetrahydrofuran at room temperature, and compound 2 was synthesized by Pd-catalyzed cross-coupling of I with 4-I-C6H4B(Mes)2. Both organoborane compounds 1 and 2 have been characterized by infrared spectroscopy, NMR spectroscopy, and mass spectrometry. The molecular structures of I and 1 were confirmed by X-ray crystallography. The electronic absorption and redox properties of 1 and 2 were investigated. They both exhibit large positive solvatochromism and their emission spectra have been recorded in a range of organic solvents with the fluorescence maxima exhibiting large bathochromic shifts in highly polar solvents, indicative of charge transfer which leads to large dipole moments in the excited state. The application of 1 as a blue fluorescent dopant in doped guest–host organic light-emitting diodes is also described.

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Highly Efficient Organic Light-Emitting Diodes with Phosphorescent Emitters Having High Quantum Yield and Horizontal Orientation of Transition Dipole Moments

Advanced Materials ◽

10.1002/adma.201305733 ◽

2014 ◽

Vol 26 (23) ◽

pp. 3844-3847 ◽

Cited By ~ 227

Author(s):

Kwon-Hyeon Kim ◽

Chang-Ki Moon ◽

Jeong-Hwan Lee ◽

Sei-Yong Kim ◽

Jang-Joo Kim

Keyword(s):

Quantum Yield ◽

Light Emitting Diodes ◽

Dipole Moments ◽

Organic Light Emitting Diodes ◽

High Quantum Yield ◽

Transition Dipole ◽

Light Emitting ◽

Horizontal Orientation ◽

Organic Light ◽

Transition Dipole Moments

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Highly effective organic light-emitting diodes containing thermally activated delayed fluorescence emitters with horizontal molecular orientation

RSC Advances ◽

10.1039/d0ra07865d ◽

2020 ◽

Vol 10 (70) ◽

pp. 42897-42902

Author(s):

Chan Hee Lee ◽

Shin Hyung Choi ◽

Sung Joon Oh ◽

Jun Hyeon Lee ◽

Jae Won Shim ◽

...

Keyword(s):

Dipole Moments ◽

Delayed Fluorescence ◽

Organic Light Emitting Diodes ◽

Host Matrix ◽

Transition Dipole ◽

Thermally Activated Delayed Fluorescence ◽

Light Emitting ◽

Thermally Activated ◽

Organic Light ◽

Transition Dipole Moments

The linear D–A–D type of molecular structure of AcPYM and PxPYM enhances the horizontally oriented alignment and up to 87% of the horizontal transition dipole moments in the host matrix is realized.

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Correlating Optical and Electrical Dipole Moments To Pinpoint Phosphorescent Dye Alignment in Organic Light-Emitting Diodes

ACS Applied Materials & Interfaces ◽

10.1021/acsami.8b08963 ◽

2018 ◽

Vol 10 (37) ◽

pp. 31541-31551 ◽

Cited By ~ 13

Author(s):

Thomas Morgenstern ◽

Markus Schmid ◽

Alexander Hofmann ◽

Markus Bierling ◽

Lars Jäger ◽

...

Keyword(s):

Light Emitting Diodes ◽

Dipole Moments ◽

Organic Light Emitting Diodes ◽

Light Emitting ◽

Electrical Dipole ◽

Organic Light

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Calculating transition dipole moments of phosphorescent emitters for efficient organic light-emitting diodes

Physical Chemistry Chemical Physics ◽

10.1039/c9cp01045a ◽

2019 ◽

Vol 21 (19) ◽

pp. 9740-9746

Author(s):

Mohammad Babazadeh ◽

Paul L. Burn ◽

David M. Huang

Keyword(s):

Dipole Moment ◽

Quantum Chemical ◽

Dipole Moments ◽

Molecular Geometry ◽

Transition Dipole Moment ◽

Organic Light Emitting Diodes ◽

Transition Dipole ◽

Light Emitting ◽

Organic Light ◽

Transition Dipole Moments

Quantum-chemical calculations show that the direction of the transition dipole moment of organometallic phosphorescent emitters is sensitive to molecular geometry.

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Dipole moments and molecular structure. Part II.—The trichlorides of the elements of group V

Proceedings of the Royal Society of London. Series A, Containing Papers of a Mathematical and Physical Character ◽

10.1098/rspa.1932.0079 ◽

1932 ◽

Vol 136 (829) ◽

pp. 256-263 ◽

Cited By ~ 10

Keyword(s):

Molecular Structure ◽

Carbon Tetrachloride ◽

Dipole Moments ◽

Inorganic Compounds ◽

Antimony Trichloride ◽

Molecular Structures ◽

Polar Solvents ◽

Group V ◽

Gaseous State ◽

Analogous Data

Although numerous investigators have carried out measurements of the dipole moments of the commoner organic compounds, few references are to be found to analogous data for inorganic compounds. The latter are confined almost exclusively to those substances which can be investigated in the gaseous state. The present series of investigations were commenced, therefore, with a view to applying the method of dilute solutions to the measurement of the dipole moments of such inorganic compounds as are soluble in non-polar solvents, and to relating the dipole moments of analogous groups of compounds to their molecular structures. The first series of measurements to be made, and those described in this paper, were upon the trichlorides of phosphorus, arsenic and antimony. Of these, measurements had been recorded only with respect to antimony trichloride when this investigation was carried out. More recently, measurements of the dipolar moments of all three compounds have been recorded by Bergmann and Engel. but their experimental results show much greater discrepancies among one another than do those of the author. Werner used both benzene and ethyl ether as solvents for the antimony trichloride, finding a considerable difference between the values obtained in the two cases. Bergmann and Engel used carbon tetrachloride as solvent for the phosphorus and arsenic trichlorides and benzene for the antimony trichloride. In the present investigation, benzene has been used as the solvent for all three compounds.

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