Trifluoromethyl benzimidazole-based conjugated polymers with deep HOMO levels for organic photovoltaics

Shim, Joo Young; Kim, Taehyo; Kim, Juae; Kim, Jin-Woo; Kim, Il; Kim, Jin Young; Suh, Hongsuk

doi:10.1016/j.synthmet.2015.03.034

Cited by 16 publications

(7 citation statements)

References 27 publications

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“…CF 2 adducts, however,s howe xactly opposite behavior:t hey give rise to homofullerene structures where additions ites remain in the p-system.T his gives rise to am ore strongly bound LUMO, [4] which can be advantageous ford oping of semiconductor polymers with deeper HOMO levels. [5] In difluoromethylenated fullerenes, in agreement with Bent's rule, highly electronegative fluorine atoms dictate increased contributions of carbona tom porbitals to the CÀFb onds and, accordingly, highers orbital contributions to the F 2 CÀC cage bond. [6] As ar esult,t he CÀCF 2 ÀCa ngle tends to increase and the CÀCb ond that bears the CF 2 moiety becomes cleaved, in contrastw ith the case of less electronegative CX 2 adducts with X = H, Cl, Br,o rI .…”

Section: Introductionmentioning

confidence: 55%

Stepwise Regioselective Hydrogenation of cis‐2‐C₆₀(CF₂)₂ Homofullerene with [6,6]‐Open/Closed Valence Tautomerism

Bogdanov

Semivrazhskaya

Belov

et al. 2016

Chemistry A European J

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The homofullerene compound cis-2-C (CF ) , which has an unusual kind of open/closed valence tautomerism undergoes consecutive regioselective hydrogenation at bridgehead carbon atoms upon reduction with Zn/Cu couple in H O-toluene mixture. The tautomerism barrier in cis-2-C (CF ) is negligible in the neutral state, whereas negative charging both impedes tautomeric transformation and promotes regioselective addition of electrophilic species at the bridgehead carbon atoms. In light of this observation, two novel homofullerene derivatives, mixed [6,6]-open/closed C (CF ) H and [6,6]-open cis-2-C (CF ) H , were synthesized and their structures were unambiguously determined by means of single crystal X-ray crystallography and NMR spectroscopy.

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Section: Introductionmentioning

confidence: 55%

Stepwise Regioselective Hydrogenation of cis‐2‐C₆₀(CF₂)₂ Homofullerene with [6,6]‐Open/Closed Valence Tautomerism

Bogdanov

Semivrazhskaya

Belov

et al. 2016

Chemistry A European J

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“…The polymer solution was prepared by dissolving 0.6 mg of each polymer in 1 ml of dimethyl sulfoxide (DMSO). It is known from literature that the absorption bands in the UV region can be ascribed to the and transitions of delocalized excitons in the polymer chain, whereas the absorption bands in the visible range are assigned to intramolecular charge transfer (ICT) between electron-rich moieties and electron-deficient moieties in the main chain [ 14 – 17 , 20 ]. The absorption coefficient spectra (Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, spectroscopic, electrochemical and photophysical properties of high band gap polymers for potential applications in semi-transparent solar cells

Amin¹,

Ketuly

Saeed³

et al. 2021

BMC Chemistry

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Background The design of new polymers able to filter the electromagnetic spectrum and absorb distinctly in the UV and high-energy part of visible spectrum is crucial for the development of semi-transparent solar cells. Herein, we report on the synthesis and spectroscopic, electrochemical, and photophysical characteristics of three new polymers, namely (i) Poly(triamterene-co-terephthalate), (ii) Poly[triamterene-co- 3-(2-pyridyl)-5,6-diphenyl-1,2,4-triazine-p,p′-disulfonamide], and (iii) Poly(5-hydroxyindole-2-carboxylate) that might show promise as materials for semi-transparent solar cells. Results The energy band gap, refractive index, dielectric constant, and optical conductivity of the electron donor polymer, poly(triamterene-co-terephthalate), were determined to be 2.92 eV, 1.56, 2.44 and 2.43 × 104 S cm−1, respectively. The synthesized electron acceptor polymers showed a relatively high refractive index, dielectric constant, and optical conductivity. The presence of a direct allowed transition was confirmed between intermolecular energy bands of the polymers. Conclusions The polymers showed relatively high energy gap and deep HOMO levels, making them strong absorbers of photons in the UV region and high energy part of the visible region. The synthesized donor and acceptors performed well relative to P3HT and fullerenes due to the close match of the HOMO and LUMO levels. With further development, the polymers could be viable for use as the active layers of semi-transparent solar cells.

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“…Despite the fact that intramolecular charge transfer (ICT) occurs at the main polymer chains between an electron deficient and an electron rich moiety due to visible absorption, it is also well known that the ππ* and n − π*transitions of delocalized excitons occur in the polymer chain due to UV absorption. (Wang, et al, 2018;Shim, et al, 2015;Kim, et al, 2018). The absorption coefficient spectra of the polymers were determined using the following equation (Alsoghier, et al, 2018;Amin, et al, 2021):…”

Section: A Photophysical Propertiesmentioning

confidence: 99%

Optical and Optoelectronic Studies of Binary and Ternary Films of Poly(L-Tryptophane), Poly(5-hydroxy-L-tryptophane), and P(TER-CO-TRI) Doped with Sudan Dye

Rahim

Amin²,

Muhammadsharif

et al. 2023

ARO

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In this work, the optical properties and optoelectronics parameters of binary and ternary composite films made of two electron acceptors, poly(L-Tryptophane) and poly(5-hydroxy-L-Tryptophane), with an electron donor, P(TER-CO-TRI), doped with Sudan dyes, are comprehensively investigated. The films with different volumetric ratios of the components were deposited onto the glass substrates using spin coating technique. Results showed that with the help of dye doping into the binary systems of poly(L-Tryptophane):P(TRI-co-TER) (1:2) and poly(5-hydroxy-L-Tryptophane):P(TRI-co-TER)(1:2), the refractive index was increased from 2.01 to 2.32. The nature of the electronic transition in the studied films was found to be a direct allowed transition, which was derived from Tauc’s equation. The combination of Cyclic voltammetry (CV) technique and absorption spectroscopy was used to determine the molecular energy levels, HOMO and LUMO of the polymer samples. It was seen that the mixture of poly(L-Tryptophane):P(TRI-co-TER):Sudan dye (1:2:2) has led to increase the energy gap to 2.95 eV and the real optical conductivity ( ) to about 433.11 S.cm-1. According to the findings, the investigated polymers can have a great potential for semitransparent organic solar cells.

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Trifluoromethyl benzimidazole-based conjugated polymers with deep HOMO levels for organic photovoltaics

Cited by 16 publications

References 27 publications

Stepwise Regioselective Hydrogenation of cis‐2‐C₆₀(CF₂)₂ Homofullerene with [6,6]‐Open/Closed Valence Tautomerism

Stepwise Regioselective Hydrogenation of cis‐2‐C₆₀(CF₂)₂ Homofullerene with [6,6]‐Open/Closed Valence Tautomerism

Synthesis, spectroscopic, electrochemical and photophysical properties of high band gap polymers for potential applications in semi-transparent solar cells

Optical and Optoelectronic Studies of Binary and Ternary Films of Poly(L-Tryptophane), Poly(5-hydroxy-L-tryptophane), and P(TER-CO-TRI) Doped with Sudan Dye

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Trifluoromethyl benzimidazole-based conjugated polymers with deep HOMO levels for organic photovoltaics

Cited by 16 publications

References 27 publications

Stepwise Regioselective Hydrogenation of cis‐2‐C60(CF2)2 Homofullerene with [6,6]‐Open/Closed Valence Tautomerism

Stepwise Regioselective Hydrogenation of cis‐2‐C60(CF2)2 Homofullerene with [6,6]‐Open/Closed Valence Tautomerism

Synthesis, spectroscopic, electrochemical and photophysical properties of high band gap polymers for potential applications in semi-transparent solar cells

Optical and Optoelectronic Studies of Binary and Ternary Films of Poly(L-Tryptophane), Poly(5-hydroxy-L-tryptophane), and P(TER-CO-TRI) Doped with Sudan Dye

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Stepwise Regioselective Hydrogenation of cis‐2‐C₆₀(CF₂)₂ Homofullerene with [6,6]‐Open/Closed Valence Tautomerism

Stepwise Regioselective Hydrogenation of cis‐2‐C₆₀(CF₂)₂ Homofullerene with [6,6]‐Open/Closed Valence Tautomerism