Small molecular non-fullerene acceptors based on naphthalenediimide and benzoisoquinoline-dione functionalities for efficient bulk-heterojunction devices

Srivani, Doli; Gupta, Akhil; La, Duong Duc; Bhosale, Rajesh S.; Puyad, Avinash L.; Xiang, Wanchun; Li, Jingliang; Bhosale, Sheshanath V.; Bhosale, Sidhanath V.

doi:10.1016/j.dyepig.2017.04.014

Cited by 19 publications

(9 citation statements)

References 42 publications

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“…[22,23] Incorporation of electron-withdrawing subunits at the core of NDIs has been shown to significantly improve the efficiency of BHJ devicesi f blendedw ith the conventional donorp olymer P3HT. [24][25][26][27][28] The enhanced efficiency of the new targetsc ontaining an NDI core is mainly due to extended conjugation,anincreaseinlight-harvesting, and intermolecular p-p stacking. Concurrently, NDIfullerenedyads with fullerene conjugated at the imide position have been investigated for photoinduced charges eparation.…”

Section: Introductionmentioning

confidence: 99%

A Triphenylamine–Naphthalenediimide–Fullerene Triad: Synthesis, Photoinduced Charge Separation and Solution‐Processable Bulk Heterojunction Solar Cells

et al. 2017

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An ew naphthalenediimide (NDI) derivative linked to triphenylamine (TPA) and fullerene (TPA-NDI-C 60 triad; S3)w as designed, synthesized and characterized. Femtosecond laser transienta bsorption spectralm easurements revealed that fast electron transfer from TPAt ot he singlet-excited state of NDI occurredt of orm ac harge-separated state (TPAC + -NDIC À -C60) with ar ate constanto fa pproximately 10 12 s À1,f ollowed by the charge-shift reaction from NDIC À to C 60 to produce the charge-separated state (TPAC + -NDI-C 60 C À ) that decayed by back electron transfer with ar ate constant of 4.4 10 9 s À1 (with ac orresponding lifetime of 230 ps). Organic bulk heterojunction solar cells were fabricatedu sing the triad S3 as an n-type semiconductor along with the conventional donorp olymer poly(3-hexylthiophene). The power conversion efficiency reached 3.03 %b efore annealing and 4.85 %a fter annealing in the optimized devices. To rationalize the performance of these organic photovoltaic devices, atomic force microscopy was used to study the morphology of poly(3-hexylthiophene):S3 blend surfaces, which were found to be well interlaced and free from projections, lumps,ori ndentations.

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Section: Introductionmentioning

confidence: 99%

A Triphenylamine–Naphthalenediimide–Fullerene Triad: Synthesis, Photoinduced Charge Separation and Solution‐Processable Bulk Heterojunction Solar Cells

et al. 2017

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“…On the contrary, sulfur substituents increased the J sc and achieved a PCE of 2.8% in star-shaped molecule with PBDTTT-EFT as the electron donor. Srivani et al [113] designed and synthesized two novel molecules, NDI-N1 ( B20 ) and NDI-N2 ( B21 ). B21 had thiophane bridge linked the NDI core and the terminal group.…”

Section: Naphthaldiimide (Ndi) Acceptorsmentioning

confidence: 99%

“…http://engine.scichina.com/doi/10.1016/j.jechem.2017.11.028 Reprinted from Ref. [113] with permission from Elsevier.…”

Section: Naphthaldiimide (Ndi) Acceptorsmentioning

confidence: 99%

Non-fullerene small molecule electron acceptors for high-performance organic solar cells

Lin

Wang

2018

Journal of Energy Chemistry

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“…Thiophenes are abundant in pharmaceuticals and natural products. In addition, they are useful intermediates for preparing novel conducting polymers and nonlinear optical materials as well as for isosteric replacement of phenyl groups in medicinal chemistry [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Cyclocondensation of the 4,4,4-Trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)-1-butanone with Hydroxylamine and Hydrazine

Flores

Kuhn

Flores

et al. 2018

Journal of Spectroscopy

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The synthesis of 4,4,4-trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)butan-1-one (3) through acylation of 1,1-dimethoxy-1-(thien-2-yl)propane (1) with trifluoroacetic anhydride and its reactions with hydroxylamine and hydrazine was investigated. X-ray structural analysis of new trifluoromethyl-substituted dielectrophile 3 revealed that this hydrate exists as a racemate with inter- and intramolecular O-H·O bonds. The crystal structure shows alignment along axis b of pair molecules with the same configuration of the O2-H·O1 bond. For 5(3)-trifluoromethyl-4-methyl-3(5)-(thien-2-yl)-1H-pyrazole (4), obtained via cyclocondensation of precursor 2 and hydrazine hydrochloride, X-ray structural analysis indicated that its rings are almost planar (torsion angle N2-C5-C6-C7–5.4°) and that S1 at the thienyl moiety is anti-periplanar to N2 (torsion angle N2-C5-C6-S1 176.01); no disorder effect was observed for the thienyl ring.

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Small molecular non-fullerene acceptors based on naphthalenediimide and benzoisoquinoline-dione functionalities for efficient bulk-heterojunction devices

Cited by 19 publications

References 42 publications

A Triphenylamine–Naphthalenediimide–Fullerene Triad: Synthesis, Photoinduced Charge Separation and Solution‐Processable Bulk Heterojunction Solar Cells

A Triphenylamine–Naphthalenediimide–Fullerene Triad: Synthesis, Photoinduced Charge Separation and Solution‐Processable Bulk Heterojunction Solar Cells

Non-fullerene small molecule electron acceptors for high-performance organic solar cells

Synthesis, Structure, and Cyclocondensation of the 4,4,4-Trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)-1-butanone with Hydroxylamine and Hydrazine

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