Donor–acceptor–donor (D–A–D) molecules based on isoindigo as active material for organic solar cells

Yassin, Ali; Leriche, Philippe; Allain, Magali; Roncali, Jean

doi:10.1039/c2nj40879a

Cited by 61 publications

(45 citation statements)

References 34 publications

(26 reference statements)

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“…Low-Bandgap Small Molecules Based on Isoindigo. Isoindigo, which has been used in the dye industry for a long time, has some advantages similar to DPP such as strong electron-withdrawing ability, low HOMO levels, and 127 However, the photovoltaic device based on this molecule gave very poor performances (PCE = 0.01%), suggesting that the hydrogen bonding locks the molecular packing into an organization unfavorable for efficient exciton diffusion and/or charge transport. Yang et al design an isoindigo-based low bandgap small molecule (S10) by introducing the rigid and coplanar thieno[3,2-b]thiophene (TT) unit.…”

Section: Chemical Reviewsmentioning

confidence: 98%

Low-Bandgap Near-IR Conjugated Polymers/Molecules for Organic Electronics

et al. 2015

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Section: Chemical Reviewsmentioning

confidence: 98%

Low-Bandgap Near-IR Conjugated Polymers/Molecules for Organic Electronics

et al. 2015

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“…The selected precursor ions were further analysed by MS/MS analysis under the following conditions: isolation width m/z = 4, collision amplitude 0.7-1.0 V (depending on the precursor ion stability), temperature of drying gas 330°C, APCI temperature 400°C, tuning parameter compound stability 100%, nitrogen flow rate 4 ml min À1 , and nitrogen pressure 45 psi. 1 H and 13 C NMR spectra were recorded on an Advance II 500 spectrometer (Bruker, USA) at 500 and 125 MHz respectively. The samples were dissolved in hexadeuteriodimethylsulfoxide.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (500 MHz, DMSO-d 6 ) d, ppm: 1.13 (3H, t, J = 7.1 Hz, CH 3 ), 4.13 (2H, q, J = 7.1 Hz, CH 2 ), 6.87 (1H, d, J = 7.75 Hz, isatin CH proton), 7.04 (1H, t, J = 7.5 Hz, isatin CH proton), 7.37 (1H, t, J = 7.6 Hz, isatin CH proton), 7.52-7.61 (3H, m, phenyl 39 CH protons), 7.73 (2H, d, J = 6.5 Hz, phenyl 29 CH protons), 8.86 (1H, d, J = 7.85 Hz, isatin CH proton), 10.77 (1H, s, NH isatin), and 11.24 (1H, s, NH pyrrolinone). 13 …”

Section: Synthesis and Analyticsmentioning

confidence: 97%

“…Red powder of the product was formed and purified by recrystallisation from ethanol in 91% yield. 1 Ethyl (4E)-1-(2-ethoxy-2-oxoethyl)-4-[1-(2-ethoxy-2-oxoethyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-5-oxo-2-thienyl-4,5-dihydro-1H-pyrrole-3-carboxylate (IIc)…”

Section: Synthesis and Analyticsmentioning

confidence: 99%

“…Dark-red powder of product IIa was formed and purified by recrystallisation from ethanol (1.3 g) in 92% yield. 1 The substance was prepared in the same way as described above for IIa. Red powder of the product was formed and purified by recrystallisation from ethanol in 91% yield.…”

Section: Synthesis and Analyticsmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, characterisation, and applications of isoindigo/Pechmann dye heteroanalogue hybrid dyes on polyester fabric

Aysha

El‐Sedik

Mashaly

et al. 2015

Coloration Technology

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A series of new dyes based on the N-analogue of Pechmann hybrid dyes were prepared by the condensation of different 5-aryl derivatives of pyrrolinone ester (phenyl, 4-bromophenyl, thienyl, and biphenyl) with isatin. N-Alkylated derivatives were also prepared using bromoethyl acetate. Full 1 H and 13 C NMR assignment was performed. All prepared dyes were soluble in most organic solvents: N-alkylated derivatives had better solubility than non-alkylated derivatives. The UV-vis absorption spectra of the derivatives under study are quite similar and exhibit maxima in the 509-526 nm range. No E/Z photoisomerisation is observed. The dyeing process, dye exhaustion on polyester, and the fastness properties of the dyes were examined.

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Enhancement in Organic Photovoltaic Efficiency through the Synergistic Interplay of Molecular Donor Hydrogen Bonding and π‐Stacking

Shewmon

Watkins

Galindo

et al. 2015

Adv Funct Materials

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For organic photovoltaic (OPV) cells based on the bulk heterojunction (BHJ) structure, it remains challenging to rationally control the degree of phase separation and percolation within blends of donors and acceptors to secure optimal charge separation and transport. Reported is a bottom‐up, supramolecular approach to BHJ OPVs wherein tailored hydrogen bonding (H‐bonding) interactions between π‐conjugated electron donor molecules encourage formation of vertically aligned donor π‐stacks while simultaneously suppressing lateral aggregation; the programmed arrangement facilitates fine mixing with fullerene acceptors and efficient charge transport. The approach is illustrated using conventional linear or branched quaterthiophene donor chromophores outfitted with terminal functional groups that are either capable or incapable of self‐complementary H‐bonding. When applied to OPVs, the H‐bond capable donors yield a twofold enhancement in power conversion efficiency relative to the comparator systems, with a maximum external quantum efficiency of 64%. H‐bond promoted assembly results in redshifted absorption (in neat films and donor:C60 blends) and enhanced charge collection efficiency despite disparate donor chromophore structure. Both features positively impact photocurrent and fill factor in OPV devices. Film structural characterization by atomic force microscopy, transmission electron microscopy, and grazing incidence wide angle X‐ray scattering reveals a synergistic interplay of lateral H‐bonding interactions and vertical π‐stacking for directing the favorable morphology of the BHJ.

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Donor–acceptor–donor (D–A–D) molecules based on isoindigo as active material for organic solar cells

Cited by 61 publications

References 34 publications

Low-Bandgap Near-IR Conjugated Polymers/Molecules for Organic Electronics

Low-Bandgap Near-IR Conjugated Polymers/Molecules for Organic Electronics

Synthesis, characterisation, and applications of isoindigo/Pechmann dye heteroanalogue hybrid dyes on polyester fabric

Enhancement in Organic Photovoltaic Efficiency through the Synergistic Interplay of Molecular Donor Hydrogen Bonding and π‐Stacking

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