New low band gap 2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole and benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole based conjugated polymers for organic photovoltaics

Murali, M. G.; Rao, Arun D.; Ramamurthy, Praveen C.

doi:10.1039/c4ra08214a

Cited by 22 publications

(15 citation statements)

References 59 publications

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“…[ 54‐57 ] The aforesaid calculations were implemented for a single repeating monomeric unit of the polymeric materials VPPy 1‐3 , and to further simplify our calculations, the long alkyl groups were substituted with methyl groups. [ 58 ] The optimized geometries of the single monomeric units of the VPPy 1‐3 , as obtained from their simulations are presented in Figure 8, along with electron density delocalization at their HOMO‐LUMOs and their obtained data are tabulated in Table 3. As got from the results, the HOMOs of polymeric materials VPPy 1‐3 are −6.13 eV ( VPPy 1 ), −5.37 eV ( VPPy 2 ), and −5.47 eV ( VPPy 3 ); whereas their LUMOs are −2.44 eV ( VPPy 1 ), −2.04 eV ( VPPy 2 ), and −2.14 eV ( VPPy 3 ).…”

Section: Resultsmentioning

confidence: 99%

Nicotinonitrile centered luminescent polymeric materials: Structural, optical, electrochemical, and theoretical investigations

Pilicode

Naik

Adhikari

2020

Polymer Engineering & Sci

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Herein, we describe the design, synthesis, and structural characterization of three new push-pull type conjugative polymers, that is, VPPy 1-3 comprising strong electron-withdrawing N-heterocyclic nicotinonitrile scaffold coupled with electron-donating phenylene units through vinylene bridges, as promising candidates for optoelectronic applications. They were successfully synthesized from their respective co-monomers by simple polycondensation synthetic routes, viz. Knoevenagel and Wittig reactions. All the polymers were subjected to photophysical, electrochemical, thermal, and theoretical studies in order to ascertain their suitability in polymer light-emitting diode applications as blue emitters. Evidently, they are readily soluble in most of the organic solvents, enabling them easy solution-processable. These new polymers display strong blue photoluminescence at the peak in the range of 431 to 462 nm with a wide optical bandgap in the order of 2.55 to 2.63 eV. The obtained electrochemical data were employed to evaluate their HOMO/LUMOs. The density functional theory calculations generated useful information on their FMO, molecular geometries, and electronic properties. Also, the influence of their structural modification on the above-said properties was discussed in detail to reveal the structure-property relationship. Conclusively, these results illustrate the great prospective of this class of polymeric materials for the application in solutionprocessable blue LEDs.

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Section: Resultsmentioning

confidence: 99%

Nicotinonitrile centered luminescent polymeric materials: Structural, optical, electrochemical, and theoretical investigations

Pilicode

Naik

Adhikari

2020

Polymer Engineering & Sci

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“…To understand the electron density distributions in the FMOs energies, DFT simulations were performed for all the polymers using Turbomole 7.2V software at the B3LYP/TZVP level 46‐49 . The calculations were performed for Py 1‐4 , considering only a single repeating monomeric unit of polymers and further to simplify the calculations, all the solubilizing alkyl groups were substituted with methyl groups 50 . The molecular geometries of a single repeating monomeric unit of polymers were first optimized with semi empirical AM1/COSMO basis using MOPAC in Tmolex 51,52 .…”

Section: Resultsmentioning

confidence: 99%

“…[46][47][48][49] The calculations were performed for Py 1-4 , considering only a single repeating monomeric unit of polymers and further to simplify the calculations, all the solubilizing alkyl groups were substituted with methyl groups. 50 The molecular geometries of a single repeating monomeric unit of polymers were first optimized with semi empirical AM1/COSMO basis using MOPAC in Tmolex. 51,52 The obtained molecular geometries of the repetitive unit of the Py 1-4, as optimized from their computation studies are displayed in Figure 5, along with electron cloud distributions in their HOMO-LUMO energies.…”

Section: Theoretical Simulationsmentioning

confidence: 99%

New cyanopyridine‐based π‐conjugative poly(azomethine)s: Synthesis, characterization and electroluminescence studies

Pilicode

Naik

Nimith

et al. 2020

Polymers for Advanced Techs

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Four new Schiff-base type conjugative polymers (CPs), that is, Py 1-4 carrying a strong electron-withdrawing cyanopyridine scaffold coupled with different electrondonating aromatic/heteroaromatic moieties were synthesized from their respective co-monomers by simple poly-condensation route. They were subjected to structural, thermal, photophysical, and electrochemical characterizations and theoretical investigations in order to identify their suitability in polymer light-emitting diode (PLED) application. All these polymers showed good film-forming ability and exhibited favorable photophysical behaviors with an optical bandgap in the order of 2.54-2.68 eV. Further, their electrochemical data were used to evaluate highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels. Finally, Py 1-4 were successfully employed as blue-light emitter in the construction of new ITO/PEDOT:PSS/ Py 1-4 /Al configured light-emitting diodes (LED), and the fabricated devices demonstrated stable blue electroluminescence behavior endorsing an effective electrons injection in the PLEDs.

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“…Apart from the F atom, other strong electron‐withdrawing moieties such as sulfonyl (SO 2 ), trifluoromethyl (CF 3 ), and cyano (CN) can be incorporated into the structure of conjugated polymers to achieve noticeable improvements in the photovoltaic properties of PSCs . In particular, the CF 3 group has received considerable interest, because it not only possesses higher electron‐withdrawing capability than the F atom but also enables facile tuning of important properties including chemical stability, thermal stability, and solubility . The electronic contributions of the substituents can be expressed by their Hammett constants (σ); the corresponding values for CF 3 and F on the meta ‐position (σ p ) of benzene were calculated as 0.43 and 0.34, respectively .…”

mentioning

confidence: 99%

“…reported that CF 3 groups on the electron‐donating triphenylamine moiety in a D–A polymer can increase the V oc of the PSC up to 1.00 V . In addition, several D–A polymers with CF 3 groups on the electron‐withdrawing components have been prepared for photovoltaic applications . However, the PCEs of these CF 3 ‐containing D–A type polymers have remained less than 1.5% so far.…”

mentioning

confidence: 99%

Synthesis of Trifluoromethylated Quinoxaline‐Based Polymers for Photovoltaic Applications

Putri

Kim

Whang

et al. 2018

Macromol. Rapid Commun.

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A series of quinoxaline-based conjugated polymers, in which the electron-donating benzodithiophene (BDT) unit is linked to the electron-accepting 6,7-difluorinated quinoxaline (DFQ) derivatives by a thiophene bridge, is synthesized. To investigate their effects on the intrinsic properties of polymers, strong electron-withdrawing trifluoromethyl (CF ) groups were incorporated into the meta-position of the phenyl ring at the 2,3-positions of the DFQ unit of the reference polymer, labelled PEhB-FQx, to yield the target polymer PEhB-FQxCF3. In addition, the 2-ethylhexyloxy substituents on the BDT donor in PEhB-FQxCF3 are changed to the more planar 2-ethylhexyl thiophene units to produce another target polymer PThB-FQxCF3. Owing to the significant contributions of the CF moiety, PEhB-FQxCF3 exhibits quite discernible optical and electrochemical properties along with significant enhancement in photovoltaic performances compared to the reference polymer PEhB-FQx. Furthermore, the incorporation of the alkylthienyl side chains on the BDT moiety confers on the resultant PThB-FQxCF3 to possess the maximum power conversion efficiency of 7.26% with an open circuit voltage of 0.88 V, short-circuit current density of 12.20 mA cm , and fill factor of 67.80%.

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New low band gap 2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole and benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole based conjugated polymers for organic photovoltaics

Abstract: Novel low band gap conjugated polymers (PBDTTBIandPBDTBBT) are designed and synthesized for polymer solar cell applications.

Cited by 22 publications

References 59 publications

Nicotinonitrile centered luminescent polymeric materials: Structural, optical, electrochemical, and theoretical investigations

Nicotinonitrile centered luminescent polymeric materials: Structural, optical, electrochemical, and theoretical investigations

New cyanopyridine‐based π‐conjugative poly(azomethine)s: Synthesis, characterization and electroluminescence studies

Synthesis of Trifluoromethylated Quinoxaline‐Based Polymers for Photovoltaic Applications

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