6,7-Di(thiophen-2-yl)naphtho[2,3-c][1,2,5]thiadiazole and 4,6,7,9-tetra (thiophen-2-yl)naphtho[2,3-c][1,2,5]thiadiazole as new acceptor units for D-A type co-polymer for polymer solar cells

Ratha, Radhakrishna; Singh, Ashish; Afroz, Mohammad Adil; Gupta, Ritesh Kant; Baumgarten, Martin; Müllen, Kläus; Iyer, Parameswar Krishnan

doi:10.1016/j.synthmet.2019.04.013

Cited by 13 publications

(9 citation statements)

References 59 publications

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“…To fully cover the visible spectrum with the available emission wavelengths,w ei ntroduced ap henyl, aBTD,and an NTD core,respectively.Both BTD and NTD are widely used chromophores for conjugated polymers and provide excellent p-conjugation and aromaticity. [33][34][35][36][37][38] To identify the activated mechanofluorophores,f or determination of molar absorptivities and fluorescence quantum yields, and for concentration calibration for bond scission experiments using CLSM, control compounds 6a-c (Figure S1) resembling the activated mechanofluorophores were synthesized.…”

Section: Resultsmentioning

confidence: 99%

Multicolor Mechanofluorophores for the Quantitative Detection of Covalent Bond Scission in Polymers

et al. 2021

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The fracture of polymer materials is am ultiscale process starting with the scission of as ingle molecular bond advancing to as ite of failure within the bulk. Quantifying the bonds broken during this process remains ab ig challenge yet would help to understand the distribution and dissipation of macroscopic mechanical energy.W ehere showthe design and synthesis of fluorogenic molecular optical force probes (mechanofluorophores) covering the entire visible spectrum in both absorption and emission. Their dual fluorescent character allows to tracknon-broken and broken bonds in dissolved and bulk polymers by fluorescence spectroscopya nd microscopy. Importantly,wedevelop an approach to determine the absolute number and relative fraction of intact and cleaved bonds with high local resolution. We anticipate that our mechanofluorophores in combination with our quantification methodology will allowt oq uantitatively describe fracture processes in materials ranging from soft hydrogels to high-performance polymers.

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Section: Resultsmentioning

confidence: 99%

Multicolor Mechanofluorophores for the Quantitative Detection of Covalent Bond Scission in Polymers

et al. 2021

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“…To estimate the hole mobility (μ h ) of polymer-based blends, a device architecture comprising ITO/PEDOT:PSS/Polymer:PC 71 BM/Cu was utilized (Figure S6a). The hole mobility was calculated to be 2.1 × 10 –4 , 2.7 × 10 –4 , 2.2 × 10 –4 , and 1.5 × 10 –4 cm 2 V –1 S –1 , respectively, for PTB7-Th-, M1-, M2-, and M3-based blends using the space charge-limited current (SCLC) method (Table ). The hole mobility was enhanced for M1 and M2, which justifies the changes in the J – V profile parameters of terpolymer-based PSCs.…”

Section: Resultsmentioning

confidence: 99%

Backbone Engineering with Fluoroarene to Mitigate Morphological Disorder for High-Performance Polymer Solar Cells

Hossain

Garai

Arunagirinathan

et al. 2021

ACS Appl. Polym. Mater.

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Three random terpolymers were synthesized by subtle incorporation of fluoroarenes as the third monomer into the popular PTB7-Th backbone and utilized for photovoltaic applications. By substituting 5% of 3-fluorothieno[3,4-b]thiophene-2-carboxylate in the PTB7-Th backbone using monomers such as 2,5-difluorobenzene, 2,3-difluorobenzene, and 2,3,5,6-tetrafluorobenzene, random terpolymers M1, M2, and M3 were synthesized, respectively. The presence of fluorinated monomers deepened the highest occupied molecular orbital (HOMO) energy level of terpolymers, which substantially enhanced the open circuit voltage (V OC) of polymer solar cells (PSCs). The power conversion efficiency (PCE) for M1- and M2-based PSCs reached up to 9.48 and 8.80% from 8.19% for the PTB7-Th:PC71BM blend. However, M3-based blend exhibited an inferior PCE of 8.13% majorly due to its weaker absorption in the higher-wavelength region and lower carrier mobility. The M1 polymer also exhibited an enhanced PCE of 9.01% compared to 7.68% for PTB7-Th with ITIC, a non-fullerene acceptor. Moreover, the fluoroarenes induced intra/intermolecular non-covalent interactions in blend films. These interactions acted as a conformational lock to tune the morphology that also improved the phase domain stability. M1:PC71BM-based PSC displayed superior capability to sustain under ambient conditions and it retained 82% of its initial PCE after 1000 h of ambient exposure in comparison to 51% of the PTB7-Th blend under a relative humidity of 45 ± 5%. This generic approach can be utilized in finely modulating the property of photovoltaic materials to enhance the performance along with the stability of PSCs.

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“…Sowohl BTD als auch NTD sind weit verbreitete Chromophore für konjugierte Polymere und bieten eine ausgezeichnete p-Konjugation und Aromatizität. [33][34][35][36][37][38] Zur Identifizierung der aktivierten Mechanofluorophore, zur Bestimmung der molaren dekadischen Extinktionskoeffizienten und Fluoreszenzquantenausbeuten sowie zur Konzentrationskalibrierung für Bindungsspaltungsexperimente mittels CLSM wurden Kontrollverbindungen 6 a-c (Abbildung S1) synthetisiert, die den aktivierten Mechanofluorophoren ähneln.…”

Section: Ergebnisse Und Diskussionunclassified

Mehrfarbige Mechanofluorophore für die quantitative Anzeige kovalenter Bindungsbrüche in Polymeren

et al. 2021

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Der Bruch von Polymermaterialien ist ein multiskaliger Prozess, der mit der Spaltung einer einzelnen molekularen Bindung beginnt und sich bis zu einer Bruchstelle im Festkçrper ausbreitet. Die Quantifizierung der während dieses Prozesses gebrochenen Bindungen bleibt eine große Herausforderung, würde aber helfen, die Verteilung und Dissipation makroskopischer mechanischer Energie zu verstehen. Wir zeigen hier die Gestaltung und die Synthese von fluorogenen molekularen optischen Kraftsonden (Mechanofluorophoren), die das gesamte sichtbare Spektrum sowohl in Absorption als auch in Emission abdecken. Ihre dual-fluoreszenten Eigenschaften ermçglichen es, nicht gebrochene und gebrochene Bindungen in gelçsten Polymeren und im Festkçrper durch Fluoreszenzspektroskopie und -mikroskopie zu verfolgen. Wichtig ist, dass wir einen Ansatz entwickeln, um die absolute Anzahl und den relativen Anteil von intakten und gebrochenen Bindungen mit hoher lokaler Auflçsung zu bestimmen. Wir gehen davon aus, dass unsere Mechanofluorophore in Kombination mit unserer Quantifizierungsmethodik eine quantitative Beschreibung von Versagensprozessen in Materialien von weichen Hydrogelen bis hin zu Hochleistungspolymeren ermçglichen werden.

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6,7-Di(thiophen-2-yl)naphtho[2,3-c][1,2,5]thiadiazole and 4,6,7,9-tetra (thiophen-2-yl)naphtho[2,3-c][1,2,5]thiadiazole as new acceptor units for D-A type co-polymer for polymer solar cells

Cited by 13 publications

References 59 publications

Multicolor Mechanofluorophores for the Quantitative Detection of Covalent Bond Scission in Polymers

Multicolor Mechanofluorophores for the Quantitative Detection of Covalent Bond Scission in Polymers

Backbone Engineering with Fluoroarene to Mitigate Morphological Disorder for High-Performance Polymer Solar Cells

Mehrfarbige Mechanofluorophore für die quantitative Anzeige kovalenter Bindungsbrüche in Polymeren

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