Nonlinear optical absorption and fluorescence of phosphine-substituted bithiophenes in the violet-blue spectral region

Wang, Jianwei; Zhao, Qun; Lawson, Christopher M.; Gray, Gary M.

doi:10.1016/j.optcom.2011.02.046

Cited by 8 publications

(15 citation statements)

References 23 publications

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“…However, the NLA on a per formula unit basis was much lower for the polymers than for their molecular analogues. For example, a 1.0 M solution of 4Se exhibited 50% optical power limiting (transmittance at 50% of the original value) at a fluence of 1.1 J/cm 2 , while a 0.16 M solution of 5Se exhibited 50% optical power limiting at a fluence of 0.9 J/cm 2 . It is unclear why the NLA of the polymer was lower on a per formula basis when both contain similar 2,2′‐bithienyl‐5‐yl‐phosphonate groups, but it should be noted that similar differences are observed with molecular phosphonates with 2,2′‐bithienyl‐5‐yl‐phosphonate groups.…”

Section: Resultsmentioning

confidence: 99%

“…Our research group has recently reported that solutions of phosphine‐substituted bithiophenes and terthiophenes of the types Ph 2 P(X)(C 4 H 2 S) n P(X)Ph 2 and Ph 2 P(X)(C 4 H 2 S) n H (X = O, S, Se; n = 2, 3) show strong narrow band NLA at wavelengths across the violet‐blue spectral region . The phosphine‐substituted bithiophenes are particularly impressive because they combine strong NLA with high solubilities and high linear transmittances at wavelengths from 420 to 480 nm.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

Freeman

Martin

Totsch

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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The syntheses of a series of substituted polyphosphonates of the type [OP(X)(Ar)O(CH2)12]n (X = O, S, Se; Ar = phenyl, 2,2′‐bithienyl‐5‐yl) are reported. The trueM¯ns for the polyphosphonates range from 1.1 to 4.6 × 104 Da and are significantly higher than those previously reported for polyphosphonates synthesized via polycondensation reactions. Thermal characterization indicates that all of the polymers are in the rubbery state at room temperature and have thermal stabilities as high as 290 °C. The linear absorption spectra, emission spectra, and emission quantum yields of the 2,2′‐bithenyl‐5‐yl substituted polyphosphonates show distinct trends with respect to the chalcogen attached to the phosphorus. Solutions of these polymers show emission at wavelengths ranging from 380 to 400 nm and, depending on the choice of X, the quantum yields are considerably larger than that of 2,2′‐bithiophene. Nonlinear optical measurements of the polyphosphonates with 2,2′‐bithenyl‐5‐yl substituents show that nonlinear absorbance increases with increasing molecular weight of X. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3663–3674

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

Freeman

Martin

Totsch

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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“…18,19 We have recently reported that solutions of chalcogenophosphino-substituted oligothiophenes of the types Ph 2 P(X)-(C 4 H 2 S) n+1 P(X)Ph 2 and Ph 2 P(X)(C 4 H 2 S) n+1 H (X = O, S, Se; n = 1, 2) (Chart 1) show narrow band third-order nonlinear optical absorption (NLA) at wavelengths in the violet-blue spectral region. [20][21][22] The NLA of the first series of compounds reported, Ph 2 P(X)-substituted terthiophenes (1O and 2O-S), could only be measured in dilute solutions because of their relatively high linear absorptions in the violet-blue region. In contrast, the Ph 2 P(X)-substituted bithiophenes (3O-Se and 4O-Se), had little linear absorption in the violet-blue region.…”

Section: Introductionmentioning

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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“…We have recently reported that solutions of diphenylphosphino‐substituted oligothiophenes of the types Ph 2 P(X)T n H and Ph 2 P(X)T n P(X)Ph 2 (X = O, S, Se; T = 2,5‐C 4 H 2 S; n = 2, 3) exhibit NLA at wavelengths across the violet‐blue spectral region . The NLAs of Ph 2 P(X)T 3 H and Ph 2 P(X)T 3 P(X)Ph 2 were limited by the compounds' relatively high linear absorptions in the violet‐blue region.…”

Section: Introductionmentioning

confidence: 99%

“…This study also addresses a limitation in our previous hybrid computational/experimental studies of radiative and nonradiative lifetimes of the compounds shown in Scheme . These studies were carried out using conformations derived by geometrically optimizing the structures observed in the X‐ray crystal structures of the compounds.…”

Section: Introductionmentioning

confidence: 99%

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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Nonlinear optical absorption and fluorescence of phosphine-substituted bithiophenes in the violet-blue spectral region

Cited by 8 publications

References 23 publications

Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

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

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

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