A pentacyclic <i>S</i>,<i>N</i>-heteroacene based electron acceptor with strong near-infrared absorption for efficient organic solar cells

Chen, Xiaohan; Líu, Hao; Xia, Lixing; Hayat, Tasawar; Alsaedi, Ahmed; Tan, Zhan’ao

doi:10.1039/c9cc03536b

Cited by 24 publications

(18 citation statements)

References 23 publications

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“…For example in co‐oligomeric donor D , the SN5’ block is connected to diketopyrrolopyrrole acceptor moieties (Figure 3) leading to a PCE of 3.8 % in BHJ‐OSCs when blended with fullerene PC 71 BM [25] . The variability of the SN5’ system becomes obvious when regarding A‐D‐A system E , which combines SN5’ and DCIF acceptors [26] . These strong acceptors substantially stabilize the frontier orbitals of the A‐D‐A co‐oligomer leading to strong NIR absorption and improved 8.9 % PCE when combined as NFA with donor polymer PBDB‐T‐2F in BHJ‐OSCs.…”

Section: Introductionmentioning

confidence: 99%

“… [25] The variability of the SN5’ system becomes obvious when regarding A‐D‐A system E , which combines SN5’ and DCIF acceptors. [26] These strong acceptors substantially stabilize the frontier orbitals of the A‐D‐A co‐oligomer leading to strong NIR absorption and improved 8.9 % PCE when combined as NFA with donor polymer PBDB‐T‐2F in BHJ‐OSCs. Finally, dimesitylboron end‐capped SN5’ F showed a high fluorescence quantum yield allowing application as fluorescent probe in fluoride sensors.…”

Section: Introductionmentioning

confidence: 99%

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Advanced Acceptor‐Substituted S,N‐Heteropentacenes for Application in Organic Solar Cells

Kraus

Lucas

Wolff

et al. 2021

Chemistry A European J

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Ambifunctional heterpentacenes with the heteroatom sequence SSNSS in the ladder-type backbone were used either as donor or as nonfullerenic acceptor in solutionprocessed bulk-heterojunction solar cells. Different acceptor moieties and side chains were inserted. Synthesis and characterization of the systematically varied structural motifs provided insight in structure-property relationships. Moreover, a dimeric heteroacene was synthesized, and the optoelectronic properties were compared to those of its monomeric counterpart.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Advanced Acceptor‐Substituted S,N‐Heteropentacenes for Application in Organic Solar Cells

Kraus

Lucas

Wolff

et al. 2021

Chemistry A European J

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“…A symmetrical DSSC dye based on tetrathienopyrrole was published in 2019 by Chen et al, comprising an indenonylidene-acceptor fragment 53 (Scheme 13). 29 The synthetic approach to the formylated intermediate 52 was considerably different from the aforementioned process. Here, a dibrominated dithienopyrrole 48 was first isomerized, then formylated to give dialdehyde 49.…”

Section: Reviewmentioning

confidence: 99%

S,N-Heteropentacenes – Syntheses of Electron-Rich Anellated Pentacycles

Berens

Müller

2021

Organic Materials

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This review summarizes syntheses of S,N-heteropentacenes, i.e. electron-rich sulfur and nitrogen-embedding pentacycles, and briefly highlights selected applications in molecular electronics. Depending on the anellation mode and the number of incorporated heteroatoms, electron density can be raised by increasing nitrogen incorporation and polarizability is manifested by the sulfur content. In comparison to triacene analogues, the conjugation pathways of S,N-heteropentacenes are increased and the favorable acene-typical crystallization behavior allows for diverse application in organic electronics. Furthermore, substitution patterns allow fine-tuning the electronic properties, extending the π-systems, and supplying structural elements for further application.1 Introduction2 Thiophene-Centered S,N-Heteropentacenes2.1 Dipyrrolo-Fused Thiophenes2.2 Diindolo-Fused Thiophenes3 Pyrrole-Centered S,N-Heteropentacenes3.1 Dithieno-Fused Pyrroles3.2 Bis[1]benzothieno-Fused Pyrrole4 Fused 1,4-Thiazines4.1 Dinaphtho-Fused 1,4-Thiazines4.2 Bis[1]benzothieno-Fused 1,4-Thiazines5 Conclusions and Outlook

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“…The highly planar π-conjugated systems revealed interesting structural features such as nearly complete bond length equalization and S-S and S-π dipolar interactions in the solid state. Due to tunable optoelectronic properties, a variety of functionalized derivatives, mainly trimeric DTP (SN3) [18], pentameric SN5 [19][20][21][22][23], and hexameric SN6 [24][25][26][27][28], have been successfully implemented as active semiconducting components in organic solar cells [18][19][20][21][24][25][26], perovskite solar cells [22,27], organic field-effect transistors [28], or sensors [23]. The interesting structure-property relationships of the S,N-heteroacene series inspired as well theoretical work.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of S,N-heterotetracenes

Vogt¹,

Henne²,

Wetzel³

et al. 2020

Beilstein J. Org. Chem.

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The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep synthetic routes. A Buchwald–Hartwig amination of brominated precursors, thermolysis of azide precursors, and a Cadogan reaction of nitro-substituted precursors were successfully applied to eventually build-up pyrrole rings to stable and soluble fused systems. The various obtained heteroatom sequences ‘SSNS’ (SN4), ‘SNNS’ (SN4’’), and ‘NSSN’ (SN4’) allowed for evaluation of structure–property relationships relative to the sulfur analogue tetrathienoacene (‘SSSS’). In line with the results for the whole series of S,N-heteroacenes, we find that replacement of sulfur by nitrogen atoms in the tetra- and hexacyclic systems leads to a red-shift in absorption, a decrease in oxidation potential and energy gap. On the other hand, the replacement of a thiophene ring by benzene leads to the opposite effects.

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A pentacyclic S,N-heteroacene based electron acceptor with strong near-infrared absorption for efficient organic solar cells

Abstract: A novel non-fullerene acceptor–donor–acceptor (A–D–A) structured small molecule acceptor material with fused ring N-alkyl DTP as the central donor unit and EG-2F as the terminal acceptor unit, named DTP-C17-4F, was designed and synthesized.

Cited by 24 publications

References 23 publications

Advanced Acceptor‐Substituted S,N‐Heteropentacenes for Application in Organic Solar Cells

Advanced Acceptor‐Substituted S,N‐Heteropentacenes for Application in Organic Solar Cells

S,N-Heteropentacenes – Syntheses of Electron-Rich Anellated Pentacycles

Synthesis and characterization of S,N-heterotetracenes

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