Disperse dyes derived from 3-oxo-2,3-dihydrobenzo-[itb]thiophene-1,1-dioxide and 3-dicyanomethylene-2,3-dihydrobenzo [itb] thiophene-1,1-dioxide

Shenoy, V. U.; Patel, Vaishali P.; Seshadri, S.

doi:10.1016/0143-7208(89)85024-7

Cited by 19 publications

(8 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To compare experimental absorption with vertical excitation these two solvents were chosen because experimental absorption values in DMF and EA are available in the literature. 19 From Table 2, it is observed that vertical excitations are in the range of the experimentally obtained absorption values with small % deviation. In all the compounds, an electronic transition occurs from Highest Occupied Molecular Orbital (HOMO) to Lowest Occupied Molecular Orbital (LUMO).…”

Section: Vertical Excitation and Oscillator Strengthmentioning

confidence: 72%

See 1 more Smart Citation

Investigation of photophysical, structural aspects and nonlinear optical properties of Foron blue SR analogs using Density Functional Theory (DFT)

Bhagwat

Sekar

2019

J Chem Sci

View full text Add to dashboard Cite

Analogs of 2-[(2Z)-2-[[4-(dihexylamino)-2-methylphenyl]methylidene]-1,1-dioxo-1-benzothiophen-3-ylidene]propanedinitrile (Foron blue SR, Disperse Blue 354) are studied in terms of photophysical, structural aspects and its nonlinear optical properties evaluated by using Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TD-DFT). The structures were optimized by using function B3LYP and basis set used was 6-31G(d). Polarizability (α), first and second order hyperpolarizability (β and γ) was determined by three density functionals B3LYP, CAM-B3LYP and BHandHLYP. B3LYP functional and the basis set 6-311+G(d,p) shows high values of α, β and γ. The B3LYP functional gives the highest first order hyperpolarizability value for (Z)-2-(2-(4-(dimethylamino)benzylidene)-1,1dioxidobenzo[b]thiophen-3(2H)-ylidene)malononitrile (3a) is 373.31 × 10 −30 e.s.u and 486.32 × 10 −30 e.s.u in ethylacetate and dimethylformamide respectively. Effect of bond length alteration (BLA) and bond order alteration (BOA) on first order hyperpolarizability was evaluated. Intrinsic hyperpolarizability shows the compound (Z)-2-(4-(dimethylamino)benzylidene)benzo[b]thiophen-3(2H)-one 1,1-dioxide (1a) intrinsically good. Perturbation potential is found to decrease as absorption energy deceases and hyperpolarizability increases.

show abstract

Section: Vertical Excitation and Oscillator Strengthmentioning

confidence: 72%

“…19 by using Density Functional Theory [B3LYP/6-31G(d)] and Time Dependent Density Functional Theory [TD-B3LYP/6-31G(d)]. The structures were optimized by using function B3LYP and basis set used was 6-31G(d).…”

mentioning

confidence: 99%

Investigation of photophysical, structural aspects and nonlinear optical properties of Foron blue SR analogs using Density Functional Theory (DFT)

Bhagwat

Sekar

2019

J Chem Sci

View full text Add to dashboard Cite

show abstract

“…All other chemicals were purchased commercially and used as received. Benzo[b]thiophene-3(2H)-one 1,1-dioxide ( 1 ) was synthesized according to the literature. , IDTT-CHO was purchased from Derthon OPV Co Ltd. (Shenzhen, China) and used directly without any further purification.…”

Section: Methodsmentioning

confidence: 99%

“…33 Although benzothiophene dioxide has been used for preparing commercial dyes since 1960, its application in OSCs has yet to be explored. 35 In comparison with the commonly used end-capping unit INCN, benzothiophene dioxide is more electron-deficient due to the replacement of the ketone with a sulfonyl group. It also has a red-shifted absorption spectrum via UV−vis spectroscopy compared to INCN, and can potentially be an efficient end-capping unit to prepare NFA materials.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

End-cap Group Engineering of a Small Molecule Non-Fullerene Acceptor: The Influence of Benzothiophene Dioxide

Cao

Bauer

Pang

et al. 2018

ACS Appl. Energy Mater.

View full text Add to dashboard Cite

In this study, a sulfonyl-containing end-capping moiety, benzothiophene dioxide, was selected to prepare the nonfullerene acceptor ITBC. ITBC has an acceptor−donor− acceptor (A-D-A) structure, with indacenodithieno[3,2-b]thiophene (IDTT) as the electron-rich core moiety. The strong electron-withdrawing sulfonyl acceptor units leads to extended UV−vis absorption into the near-IR region and relatively low frontier molecular orbital energy levels (LUMO/HOMO: −4.13 eV/−5.61 eV) with a narrow bandgap of 1.48 eV. These values compare favorably to the well-studied small molecule acceptor 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile end-capped indacenodithieno[3,2-b]thiophene (ITIC). A power conversion efficiency of 4.17% was achieved by fabricating organic solar cells with the fluorinated conjugated polymer FTAZ as the donor and ITBC as the acceptor. These results indicate that benzothiophene dioxide is a novel electron-withdrawing end-capping unit for ITBC, and can be used as an electron acceptor for organic solar cells.

show abstract

ChemInform Abstract: Disperse Dyes Derived from 3‐Oxo‐2,3‐dihydrobenzo(b)thiophene 1,1‐Dioxide (II) and 3‐Dicyanomethylene‐2,3‐dihydrobenzo(b)thiophene 1,1‐Dioxide (VII).

Shenoy¹,

Patel²,

Seshadri³

1989

ChemInform

View full text Add to dashboard Cite

Disperse dyes derived from 3-oxo-2,3-dihydrobenzo-[itb]thiophene-1,1-dioxide and 3-dicyanomethylene-2,3-dihydrobenzo [itb] thiophene-1,1-dioxide

Cited by 19 publications

References 4 publications

Investigation of photophysical, structural aspects and nonlinear optical properties of Foron blue SR analogs using Density Functional Theory (DFT)

Investigation of photophysical, structural aspects and nonlinear optical properties of Foron blue SR analogs using Density Functional Theory (DFT)

End-cap Group Engineering of a Small Molecule Non-Fullerene Acceptor: The Influence of Benzothiophene Dioxide

ChemInform Abstract: Disperse Dyes Derived from 3‐Oxo‐2,3‐dihydrobenzo(b)thiophene 1,1‐Dioxide (II) and 3‐Dicyanomethylene‐2,3‐dihydrobenzo(b)thiophene 1,1‐Dioxide (VII).

Contact Info

Product

Resources

About