Novel Cyclopentadithiophene‐Based D–A Copolymers for Organic Photovoltaic Cell Applications

Drozdov, Fedor V.; Myshkovskaya, Ekaterina N.; Susarova, Diana K.; Troshin, Pavel A.; Fominykh, Olga D.; Balakina, Marina Yu.; Bakirov, Artem V.; Shcherbina, Maxim A.; Choi, Jin‐Woo; Tondelier, Denis; Бузин, М. И.; Чвалун, С. Н.; Yassar, Abderrahim; Ponomarenko, S.A.

doi:10.1002/macp.201370328

Cited by 6 publications

(5 citation statements)

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“…The synthetic routes of the three new dyes are shown in Scheme . The starting materials of 4,7-dibromobenzo[1,2,5]thiadiazole ( 1a ), 4,7-dibromo-5,6-bis(octyloxy)benzo[1,2,5]thiadiazole ( 1b ), dimethyl(4-( p -tolyl)-1,2,3,3 a ,4,8 b -hexahydrocyclopenta[ b ]indol-7-yl)boronate ( 6 ), and 4,4-dioctyl-4 H -cyclopentadithiophene ( 7 ) were synthesized according to refs – . The detailed synthetic procedures of the important intermediates were outlined in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Molecular Engineering of Quinoxaline-Based D–A−π–A Organic Sensitizers: Taking the Merits of a Large and Rigid Auxiliary Acceptor

Jiang

Islam

et al. 2018

ACS Appl. Mater. Interfaces

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The continuing efforts of creating novel D-A-π-A structured organic sensitizers with excellent optoelectronic properties have resulted in substantial improvement of power conversion efficiency (PCE) as well as stability of dye-sensitized solar cells (DSSCs). Here, we report a new molecular engineering strategy for enhancing optical gain and improving excited-state features in D-A-π-A structured organic sensitizers by improving the conjugation size and rigidity of the auxiliary acceptor functional group. A series of phenanthrene-fused-quinoxaline (PFQ)-based D-A-π-A organic sensitizers (WS-82, WS-83, and WS-84) are designed and synthesized for applications in DSSCs. Compared to 2,3-diphenylquinoxaline (DPQ)-based dye IQ-4, PFQ dyes show extended absorption spectra and improved open-circuit voltage performance. Upon a systematical engineering of alkyl chains and π-spacer structure, the unfavorable issues of PFQ dyes including low solubility and high energy barrier in intramolecular charge transition are successfully eliminated. When applied in iodine electrolyte-based DSSCs, the best performing PFQ dye WS-84 shows a PCE of 10.11%, which is much higher than that of our previous champion DPQ dye IQ-4 under the same conditions.

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Section: Methodsmentioning

confidence: 99%

Molecular Engineering of Quinoxaline-Based D–A−π–A Organic Sensitizers: Taking the Merits of a Large and Rigid Auxiliary Acceptor

Jiang

Islam

et al. 2018

ACS Appl. Mater. Interfaces

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“…[4][5][6] In particular, p-conjugated polymers have attracted considerable interest due to their simple processing, low operating voltages, quick response times, and color tuning over the entire UV-vis range, making this kind of polymers ideally suited for a wide range of optoelectronic devices. [7][8][9][10][11][12][13][14][15][16] Thus, design and synthesis of new conjugated polymers with various optoelectronic properties hold great promise in display technology area. [17][18][19] Selecting electron-donating (donor; D) and withdrawing units (acceptor; A) in an alternate mode in the polymer chain is considered to be one of the most competent methods of depreciating optical and electrochemical band gaps of conjugated polymers.…”

Section: Introductionmentioning

confidence: 99%

“…[20][21][22][23] Increasing the degree of delocalization of electrons acquired by increasing the coplanarity of structure causes the band gap to be further depreciated. 10,24 This can be attributed to intramolecular charge transfer in the excited state. However, the excited electron in such a case is supposed to be delocalized over electron-deficient segments.…”

Section: Introductionmentioning

confidence: 99%

“…4–6 In particular, π-conjugated polymers have attracted considerable interest due to their simple processing, low operating voltages, quick response times, and color tuning over the entire UV-vis range, making this kind of polymers ideally suited for a wide range of optoelectronic devices. 7–16 Thus, design and synthesis of new conjugated polymers with various optoelectronic properties hold great promise in display technology area. 17–19…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, photophysical properties, and computational studies on N-hexylphenothiazine/cyanopyridine based π-conjugated copolymers

El‐Shehawy

Attia

Abdallah

et al. 2021

High Performance Polymers

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In this paper, π-conjugated copolymers, namely N-hexylphenothiazine/cyanopyridine/phenyl/benzothiadiazole, N-hexylphenothiazine/cyanopyridine/phenyl/9,9-dihexylfluorene, and N-hexylphenothiazine/cyanopyridine/phenyl/9,9-diethylhexylfluorene were readily synthesized via Pd-catalyzed Suzuki cross-coupling reaction. The polymer structures and their photophysical properties were characterized by elemental analysis, 1H NMR, GPC, TGA, XRD, UV-vis absorption and PL spectroscopy measurements. The coupling agent effect on photophysical properties of copolymers was investigated to rationally design polymers with particular physical properties to be employed in optoelectronic devices. The UV-vis absorption spectroscopy of copolymers showed λmax at a range of ∼334–474 nm and red-shifted in their films to a range of ∼342–381 nm. These copolymers displayed highly intense fluorescence in their solutions and films. The PL spectra of copolymers indicated red and near-infrared light, rendering them a prospect for being red and near-infrared light-emitting materials for PLEDs. XRD analysis demonstrated a d-spacing range of ∼3.79–4.32 Å, reflecting π-π stacking and some degree of crystallinity in some polymers, and only P1 and P2 showed peaks in the small-angle region, indicating lamellar structures. To understand the relationship between molecular structures of target materials and their photophysical and photovoltaic properties, density functional theory (DFT) and its time-dependent form (TD-DFT) were employed.

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“…[6][7][8] Recently, we reported the synthesis of few novel cyclopentadithiophene-based polymers and their application in organic solar cells and light-emitting diodes. [9][10][11] Polycyclopentadithiophenes show low optical band gaps and undergo facile electrochemical 12 and oxidative chemical polymerization reactions. 13 Polymer and low molecular weight materials comprising 4H-cyclopenta(2,1-b:3,4-b 0 )dithiophene (CPDT) units demonstrated valuable properties and are expected to find practical applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel conjugated polymers comprising modified cyclopentadithiophene units in the main chain

Kostianovskii

Susarova

Troshin

2017

High Performance Polymers

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Novel Cyclopentadithiophene‐Based D–A Copolymers for Organic Photovoltaic Cell Applications

Cited by 6 publications

References 0 publications

Molecular Engineering of Quinoxaline-Based D–A−π–A Organic Sensitizers: Taking the Merits of a Large and Rigid Auxiliary Acceptor

Molecular Engineering of Quinoxaline-Based D–A−π–A Organic Sensitizers: Taking the Merits of a Large and Rigid Auxiliary Acceptor

Synthesis, characterization, photophysical properties, and computational studies on N-hexylphenothiazine/cyanopyridine based π-conjugated copolymers

Synthesis of novel conjugated polymers comprising modified cyclopentadithiophene units in the main chain

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