Introducing a new triazoloquinoxaline‐based fluorene copolymer for organic photovoltaics: Synthesis, characterization, and photovoltaic properties

Baran, Derya; Pasker, Felix M.; Blanc, Stephan Le; Schnakenburg, Gregor; Ameri, Tayebeh; Höger, Sigurd; Brabec, Christoph J.

doi:10.1002/pola.26465

Cited by 11 publications

(13 citation statements)

References 26 publications

(16 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There were few literature reports on triazoloquinoxaline-based polymers focusing on their photovoltaic properties when we launched this project. [34][35][36] Compared to triazoloquinoxaline, di-2-thienyltriazoloquinoxaline (BTzQx) can relieve the steric hindrance between the donor and triazoloquinoxaline, thereby increasing the hole mobility.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of triazoloquinoxaline polymers with positioning alkyl or alkoxyl chains for organic photovoltaics cells

Hai

Zhao

et al. 2014

Polym. Chem.

View full text Add to dashboard Cite

Four benzodithiophene-triazoloquinoxaline alternating polymers, PBDTT-BTzQx-EH-C1, PBDT-BTzQx-EH-C1, PBDT-BTzQx-EH-C12 and PBDT-BTzQx-C12, have been designed and synthesized to investigate the correlation of alkyl side chains with the opto-electronic properties of the resulting polymers. The introduction of side chains onto the thiophene spacer or quinoxaline unit lowers the highest occupied molecular orbital energy level of the polymers, while excessive chains prevent the polymer backbone from p-p stacking and result in a decreased short circuit current and fill factor in a photovoltaic application. The bulk heterojunction cells fabricated by blending PBDTT-BTzQx-EH-C1 with [6,6]phenyl-C61-butyric acid methyl ester exhibit a best power conversion efficiency (PCE) of 1.40%, with a short-circuit current density of 4.12 mA cm À2 , an open-circuit voltage of 0.62 V and a fill factor of 55%.The device was further optimized to 2.24% PCE by using PFN (5 nm)/Ca (5 nm) as a co-interfacial layer.

show abstract

Section: Introductionmentioning

confidence: 99%

Design and synthesis of triazoloquinoxaline polymers with positioning alkyl or alkoxyl chains for organic photovoltaics cells

Hai

Zhao

et al. 2014

Polym. Chem.

View full text Add to dashboard Cite

show abstract

“…[14] In literature, different benzotriazole derivatives were used as active layers for OPVs. In terms of optical properties PTQBDT has one of the lowest optical band gap as 1.20 eV while that of PTQF is [17] 1.40 eV, PBDT-BTzQx-C12 [16] is 1.38 eV and PFDTBTz-Q-2OC1 [13] is 1.63 eV, respectively.…”

Section: Spectroelectrochemistrymentioning

confidence: 99%

Alkyl-end phenanthroimidazole modification of benzotriazole based conjugated polymers for optoelectronic applications

et al. 2018

View full text Add to dashboard Cite

A new triazoloquinoxaline and benzodithiophene based copolymer was synthesized to investigate its electrochemical, optical and photovoltaic behaviors. According to the polymer design, combination of two acceptor units (benzotriazole and quinoxaline) which contribute imine bonds to the structure and a triazoloquinoxaline unit for enhancing electron accepting ability was pursued. As a result of electrochemical studies, the copolymer PTQBDT has a low lying HOMO energy level as −5.23 eV which increases the chemical stability of the resulting polymer and leads to a higher V oc . In addition, the copolymer has an ambipolar character with two well-defined redox couples in the n-doped state and multichromic behavior. In the context of optical studies, PTQBDT has wide absorption range in the visible region with a tail in the NIR region, which yields a low band gap of 1.20 eV. Organic photovoltaic devices were designed using PTQBDT (the electron donor) and PC 71 BM (the electron acceptor) for the preliminary studies. The resulting device exhibits a power conversion efficiency of 2.0% with a current density of 8.07 mA cm −2 , an open-circuit voltage of 0.45 V, and a fill factor of 55%. The carrier mobility of the PTQBDT was calculated as 3.00 × 10 −3 cm 2 V −1 s −1 via space-charge-limited current (SCLC) method.

show abstract

“…Semiconducting π-conjugated polymers have attracted attention in the last years as promising active hole-transporting materials, which have a wide range of applications in electro-optical devices [1–4]. Polyfluorenes (PFs) are the most often investigated semiconducting polymers and are considered promising candidate for flexible displays and blue light-emitting materials [5].…”

Section: Introductionmentioning

confidence: 99%

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

Farcas¹,

Resmeriță²,

Aubert

et al. 2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryWe report on the synthesis as well as the optical, electrochemical and morphological properties of two polyrotaxanes (4a and 4b), which consist of electron-accepting 9,9-dicyanomethylenefluorene 1 as an inclusion complex in persilylated β- or γ-cyclodextrin (TMS-β-CD, TMS-γ-CD) (1a, 1b) and methyltriphenylamine as an electron-donating molecule. They are statistically distributed into the conjugated chains of 9,9-dioctylfluorene 3 and compared with those of the corresponding non-rotaxane 4 counterpart. Rotaxane formation results in improvements of the solubility, the thermal stability, and the photophysical properties. Polyrotaxanes 4a and 4b exhibited slightly red-shifted absorption bands with respect to the non-rotaxane 4 counterpart. The fluorescence lifetimes of polyrotaxanes follow a mono-exponential decay with a value of τ = 1.14 ns compared with the non-rotaxane, where a bi-exponential decay composed of a main component with a relative short time of τ1 = 0.88 (57.08%) and a minor component with a longer lifetime of τ2 = 1.56 ns (42.92%) were determined. The optical and electrochemical band gaps (ΔE g) as well as the ionization potential and electronic affinity characterized by smaller values compared to the values of any of the constituents. AFM reveals that the film surface of 4a and 4b displays a granular morphology with a lower dispersity supported by a smaller roughness exponent compared with the non-rotaxane counterpart.

show abstract

Introducing a new triazoloquinoxaline‐based fluorene copolymer for organic photovoltaics: Synthesis, characterization, and photovoltaic properties

Cited by 11 publications

References 26 publications

Design and synthesis of triazoloquinoxaline polymers with positioning alkyl or alkoxyl chains for organic photovoltaics cells

Design and synthesis of triazoloquinoxaline polymers with positioning alkyl or alkoxyl chains for organic photovoltaics cells

Alkyl-end phenanthroimidazole modification of benzotriazole based conjugated polymers for optoelectronic applications

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

Contact Info

Product

Resources

About