The Ultraviolet Absorption Spectra of Arylphosphonic and Diarylphosphinic Acids

Jaffé, H. H.; Freedman, Leon D.

doi:10.1021/ja01124a063

Cited by 65 publications

(17 citation statements)

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“…For the majority of the compounds, the difference in the energy of the linear absorption band upon changing the phosphorus substituents is less than 5 nm with the exception of compounds Ph 2 P(O)T 2 P(O)Ph 2 and pdP(O)T 2 P(O)pd, which have a difference in absorption of 9 nm. This small effect on the energy of the linear absorption maxima with changing the phosphorus backbone substituents is consistent with the very similar linear absorption bands of phenylphosphonic acid and triphenylphosphine oxide (Δ λ max = 8 nm) implying that there is little phosphorus resonance contribution to aromatic systems ,…”

Section: Resultssupporting

confidence: 79%

Synthesis, Linear, and Nonlinear Optical Properties of Phosphonato‐Substituted Bithiophenes Derived from 2,2‐Dimethyl‐1,3‐propanediol

et al. 2017

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The synthesis, linear absorption, emission spectra, and third‐order nonlinear optical (NLO) absorptions at 430 nm of two new series of chalcogenophosphonato‐substituted bithiophenes, pdP(X)T2H and pdP(X)T2P(X)pd [pd = OCH2C(CH3)2CH2O; T = 2,5‐C4H2S; X = O, S, Se] are reported. The X‐ray crystal structures of pdP(X)T2H and pdP(X)T2P(X)pd (X = S, Se) have also been determined. The pdP(X)T2P(X)pd compounds show weak intermolecular aromatic π–π interactions while pdP(S)T2H shows S–π interactions. The compounds exhibit emission at wavelengths ranging from 380–400 nm. Some of the quantum yields are significantly larger than that of 2,2′‐bithiophene. The linear absorption spectra, emission spectra, and emission quantum yields show distinct trends with respect to the chalcogen and the number of substituents attached to the 2,2′‐bithiophene ring. NLO transmission measurements of pdP(X)T2P(X)pd (X = S, Se) indicate that saturated solutions of both compounds show significantly greater NLO absorption than saturated solutions of bpP(X)T2P(X)bp (bp = 2,2′‐biphenol, X = S, Se) do. Notably, the fluence at which the transmittance of a 0.27 m CH2Cl2 solution of pdP(Se)T2P(Se)pd falls to 50 % is 0.2 J/cm2. This rivals the best blue nonlinear absorbers in literature. The excellent emission quantum yields and NLO absorptions make these compounds promising candidates for optical power limiting and as host materials for blue OLEDs.

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Section: Resultssupporting

confidence: 79%

Synthesis, Linear, and Nonlinear Optical Properties of Phosphonato‐Substituted Bithiophenes Derived from 2,2‐Dimethyl‐1,3‐propanediol

et al. 2017

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“…This observation has been rationalized on the basis of the lack of phosphorus resonance contribution to aromatic systems. 65,66 It is somewhat surprising that the linear absorption band of the bithiophene is essentially independent of the phosphorus single bonds (i.e. P-O and P-C), yet is shifted by the changing the chalcogen attached to the phosphorus nonbonding pair of electrons.…”

Section: Paper Dalton Transactionsmentioning

confidence: 99%

Synthesis, linear and nonlinear optical properties of phosphonato-substituted bithiophenes derived from 2,2′-biphenol

et al. 2013

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Two new series of phosphonato-substituted bithiophenes, BpP(X)(C4H2S)2H and BpP(X)(C4H2S)2P(X)Bp (Bp = 2,2'-C12H8O2, X = O, S, Se), have been synthesized and characterized using linear absorption and emission spectra, and third-order nonlinear absorption measurements at 430 nm with 27 ps laser pulses. The compounds were synthesized in three steps: (1) reacting lithiated bithiophene with (Et2N)2PCl; (2) reacting the product from the first step with biphenol; and (3) reacting the product from the second step with the appropriate chalcogen. The X-ray crystal structures of two of the compounds, BpP(O)(C4H2S)2P(O)Bp and BpP(Se)(C4H2S)2P(Se)Bp, are reported and show a number of intermolecular π-π interactions. The linear absorption spectra, emission spectra, and emission quantum yields show distinct trends with respect to the chalcogen and the number of phosphorus substituents attached to the 2,2'-bithiophene ring. The compounds show emission maxima at wavelengths ranging from 380-400 nm and, BpP(S)(C4H2S)2H shows a 23-fold increase in fluorescence quantum yield relative to that of 2,2'-bithiophene. Fluorescence lifetimes and radiative and non-radiative decay rate constants for the first singlet excited state have been extracted from the quantum yields using time-dependent DFT calculations. Nonlinear transmission measurements indicate that all of the compounds show nonlinear absorption at 430 nm with 27 ps laser pulses in spite of their low solubilities. Notably, the nonlinear absorption threshold of a 0.16 mol L(-1) CH2Cl2 solution of BpP(Se)(C4H2S)2H is 0.9 J cm(-2). The excellent emission quantum yields and good nonlinear absorptions make these compounds promising candidates for optical power limiting applications and as host materials for violet-blue organic light emitting diodes.

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“…S7, ESI †). 31, 44 Forms 1a, 1b and [CuI(PPh 3 ) 1.5 ] 2 are non emissive in airequilibrated solutions and display a weak emission centered around 620 nm in air-free toluene at room temperature (f em = 2-3 ¥ 10 -3 ), with lifetimes on the order of 200-300 ns (Fig. S7, ESI † and Table 2).…”

Section: Photophysical Propertiesmentioning

confidence: 99%

Polymorph and isomer conversion of complexes based on CuI and PPh₃easily observed via luminescence

et al. 2012

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Reactions between copper(I) iodide and triphenylphosphine have been explored in solution and in the solid state and six luminescent coordination complexes have been obtained and characterized by X-ray diffraction and UV-vis spectroscopy and photophysics. Solid-state reactions of CuI with PPh(3) in different conditions (kneading, vapour digestion) and stoichiometries resulted in the formation of high ratio ligand:metal compounds while tetrameric structures could be obtained only by solution reactions. Crystal structures were determined by single crystal X-ray diffraction while purity of the bulk product was checked by powder diffraction (XRPD). Three different tetrameric structures with 1:1 stoichiometry have been synthesized: two closed cubane-type polymorphs [CuI(PPh(3))](4) (form 1a) and [CuI(PPh(3))](4) (form 1b) and an open step-like isomer [CuI(PPh(3))](4) (form 2). The conversions between the polymorphs and isomers have been studied and characterized by XRPD. The most stable form [CuI(PPh(3))](4) (form 1b) can convert into the open step-like isomer [CuI(PPh(3))](4) (form 2) in a slurry experiment with EtOH or CH(2)Cl(2) or AcCN and converts back into [CuI(PPh(3))](4)1b when exposed to vapors of toluene. At room temperature all the tetrameric compounds exhibit luminescence in the solid state and, notably, the two polymorphs show a dissimilar dual emission at low temperature. The luminescence features in the solid state seem to be peculiarly related to the presence of the aromatic phosphine ligand and depend on the Cu-Cu distance in the cluster.

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The Ultraviolet Absorption Spectra of Arylphosphonic and Diarylphosphinic Acids

Cited by 65 publications

References 0 publications

Synthesis, Linear, and Nonlinear Optical Properties of Phosphonato‐Substituted Bithiophenes Derived from 2,2‐Dimethyl‐1,3‐propanediol

Synthesis, Linear, and Nonlinear Optical Properties of Phosphonato‐Substituted Bithiophenes Derived from 2,2‐Dimethyl‐1,3‐propanediol

Synthesis, linear and nonlinear optical properties of phosphonato-substituted bithiophenes derived from 2,2′-biphenol

Polymorph and isomer conversion of complexes based on CuI and PPh₃easily observed via luminescence

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The Ultraviolet Absorption Spectra of Arylphosphonic and Diarylphosphinic Acids

Cited by 65 publications

References 0 publications

Synthesis, Linear, and Nonlinear Optical Properties of Phosphonato‐Substituted Bithiophenes Derived from 2,2‐Dimethyl‐1,3‐propanediol

Synthesis, Linear, and Nonlinear Optical Properties of Phosphonato‐Substituted Bithiophenes Derived from 2,2‐Dimethyl‐1,3‐propanediol

Synthesis, linear and nonlinear optical properties of phosphonato-substituted bithiophenes derived from 2,2′-biphenol

Polymorph and isomer conversion of complexes based on CuI and PPh3easily observed via luminescence

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Polymorph and isomer conversion of complexes based on CuI and PPh₃easily observed via luminescence