Synthesis and Characterization of Novel Red-Light-Emitting Materials with Push-Pull Structure Based on Benzo[1,2,5]thiadiazole Containing Arylamine as an Electron Donor and Cyanide as an Electron Acceptor

Ju, Jin Uk; Jung, Sung Ouk; Zhao, Qing; Kim, Yun Hi; Je, Jong Tae; Kwon, Soon Ki

doi:10.5012/bkcs.2008.29.2.335

Cited by 13 publications

(1 citation statement)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The crude stannane 4 was used without further purification. 4 and 7-bromobenzo[ c ][1,2,5]thiadiazole-4-carbaldehyde (0.14 g, 0.56 mmol) in anhydrous tetrahydrofuran (7 mL) were subjected to two freeze–pump–thaw cycles, backfilling with argon. Bis(triphenylphosphine)palladium(II) dichloride (0.16 g, 0.02 mmol) was added to the solution, and the mixture was then heated in an oil bath held at 65 °C for 4 h. The solution was allowed to cool, and the solvent was removed in vacuo .…”

Section: Methodsmentioning

confidence: 99%

Impact of Dimerization on Phase Separation and Crystallinity in Bulk Heterojunction Films Containing Non-Fullerene Acceptors

et al. 2016

View full text Add to dashboard Cite

We report the synthesis of monomeric and dimeric dicyanovinylbenzothiadiazole-based non-fullerene acceptors and investigate the phase behavior of blend systems comprising poly(3-n-hexylthiophene) (P3HT) and the new materials. Differential scanning calorimetry (DSC) thermograms of blends with different compositions revealed that no eutectic composition existed for the blends, in contrast to previously reported P3HT/ non-fullerene acceptor combinations. Analysis of the DSC data shows that the thermal properties of the P3HT and the dimeric non-fullerene acceptor are almost independent of blend composition. However, the thermal properties of blends containing the monomeric acceptor were found to depend strongly on the blend composition, with increasing concentrations of the monomeric acceptor depressing the observed melting point of the polymer. These results are complemented by specular X-ray diffraction data, which reveals stark differences in the crystallinity of the two blend systems. In the case of the dimeric acceptor, the polymer and non-fullerene molecules crystallize in a form similar to that of the neat compounds, whereas in the case of the monomeric acceptor the crystallinity of both molecules is substantially altered by the other. We then correlate the structure of the materials with the organic solar cell performance.

show abstract

Section: Methodsmentioning

confidence: 99%

Impact of Dimerization on Phase Separation and Crystallinity in Bulk Heterojunction Films Containing Non-Fullerene Acceptors

et al. 2016

View full text Add to dashboard Cite

show abstract

Significant Improvement of Dye‐Sensitized Solar Cell Performance by Small Structural Modification in π‐Conjugated Donor–Acceptor Dyes

Haid

Marszałek

Mishra

et al. 2012

Adv Funct Materials

418

253

View full text Add to dashboard Cite

Two donor-π-acceptor (D-π-A) dyes are synthesized for application in dyesensitized solar cells (DSSC). These D-π-A sensitizers use triphenylamine as donor, oligothiophene as both donor and π-bridge, and benzothiadiazole (BTDA)/cyanoacrylic acid as acceptor that can be anchored to the TiO 2 surface. Tuning of the optical and electrochemical properties is observed by the insertion of a phenyl ring between the BTDA and cyanoacrylic acid acceptor units. Density functional theory (DFT) calculations of these sensitizers provide further insight into the molecular geometry and the impact of the additional phenyl group on the photophysical and photovoltaic performance. These dyes are investigated as sensitizers in liquid-electrolyte-based dye-sensitized solar cells. The insertion of an additional phenyl ring shows significant influence on the solar cells' performance leading to an over 6.5 times higher efficiency (η = 8.21%) in DSSCs compared to the sensitizer without phenyl unit (η = 1.24%). Photophysical investigations reveal that the insertion of the phenyl ring blocks the back electron transfer of the charge separated state, thus slowing down recombination processes by over 5 times, while maintaining efficient electron injection from the excited dye into the TiO 2 -photoanode. DOI IntroductionDye-sensitized solar cells (DSSCs) are one of the most promising environmentally friendly photovoltaic devices because of their low material costs, flexiblity, and easy manufacturing processes. [ [17] gave intermediates 11 and 12 in yields of 86% and 92%, respectively. Final Knoevenagel condensation of 11 and 12 with cyanoacetic acid in the presence of ammonium acid as acceptor and anchoring group (A). Dye 1 contains the BTDA unit directly adjacent to the anchoring group, whereas dye 2 contains "only" an additional phenyl ring between both acceptor units. We investigate the influence of the structural modification of the sensitizer on optical, redox, and solar cell performance. This subtle structural change in the sensitizer induced a significant influence on the DSSCs performance. Results and Discussion SynthesisD-A dyes 1 and 2 were synthesized as shown in Scheme 1. phenyl]aniline 3 was coupled Scheme 1. Synthesis of dyes 1 and 2. a) Pd 2 (dba) 3 ·CHCl 3 , HP t Bu 3 BF 4 , 2 m aq. K 3 PO 4 (4 eq.), THF, room temperature (r.t.). b) (i) n -BuLi, THF, -78 °C (ii) Bu 3 SnCl. c) K 2 CO 3 , 1,4-dioxane/water, reflux, 1 h. 350 to 800 nm (Figure 1a). All data are summarized in Table 1. The bands at 395 nm (dye 1) and 392 nm (dye 2) correspond to the π-π * transition of the conjugated system. The longest wavelength absorption of dye 2 (λ max = 515 nm) is assigned to a charge transfer (CT) transition and is significantly blue-shifted compared to the CT-band of dye 1 (λ max = 570 nm). Furthermore, the intensity and molar extinction coefficient for the CT transition of dye 2 (ε = 29,400 L mol) is increased by a factor of 1.6 compared to dye 1 (ε = 18,900 L mol). The emission maxima of dyes 1 and 2 can be found at 681 and 665 nm, respect...

show abstract

Tuning the Optoelectronic Properties of Nonfullerene Electron Acceptors

et al. 2014

View full text Add to dashboard Cite

Broad spectral coverage over the solar spectrum is necessary for photovoltaic technologies and is a focus for organic solar cells. We report a series of small-molecule, nonfullerene electron acceptors containing the [(benzo[c][1,2,5]thiadiazol-4-yl)methylene]malononitrile unit as a high electron affinity component. The optoelectronic properties of these molecules were fine-tuned with the objective of attaining strong absorption at longer wavelengths by changing the low-ionization-potential moiety. The electron-accepting function of these materials was investigated with poly(3-n-hexylthiophene) (P3HT) as a standard electron donor. Significant photocurrent generation in the near infrared region, with an external quantum yield reaching as high as 22 % at 700 nm and an onset >800 nm was achieved. The results support efficient hole transfer to P3HT taking place after light absorption by the acceptor molecules. A Channel II-dominated power conversion efficiency of up to 1.5 % was, thus, achieved.

show abstract

Synthesis and Characterization of Novel Red-Light-Emitting Materials with Push-Pull Structure Based on Benzo[1,2,5]thiadiazole Containing Arylamine as an Electron Donor and Cyanide as an Electron Acceptor

Cited by 13 publications

References 15 publications

Impact of Dimerization on Phase Separation and Crystallinity in Bulk Heterojunction Films Containing Non-Fullerene Acceptors

Impact of Dimerization on Phase Separation and Crystallinity in Bulk Heterojunction Films Containing Non-Fullerene Acceptors

Significant Improvement of Dye‐Sensitized Solar Cell Performance by Small Structural Modification in π‐Conjugated Donor–Acceptor Dyes

Tuning the Optoelectronic Properties of Nonfullerene Electron Acceptors

Contact Info

Product

Resources

About