Dimesitylboron Endcapped S,N-Heteroacenes: Syntheses, Photophysical and Fluoride-binding Properties

Meng, Linghao; Xia, Debin; Yi, Xiaoqing; Ding, Fangwei; Fan, Rongwei; Yang, Yulin

doi:10.1246/cl.200290

Cited by 4 publications

(7 citation statements)

References 21 publications

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“…Finally, dimesitylboron end-capped SN5' F showed a high fluorescence quantum yield allowing application as fluorescent probe in fluoride sensors. [27] In continuation of our work on heteroacenes and their application in organic solar cells, we now report the further development of SN5' derivatives with systematically varied structural motifs leading to valuable structure-property relationships. The thereby tunable frontier orbital energies of these novel functionalized S,N-heteropentacenes SN5' allow for a rare two-fold application: either their implementation as donor in solution-processed BHJ-OSCs or as NFA.…”

Section: Introductionmentioning

confidence: 92%

“…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 [27] …”

Section: Introductionmentioning

confidence: 99%

“…Finally, dimesitylboron end‐capped SN5’ F showed a high fluorescence quantum yield allowing application as fluorescent probe in fluoride sensors. [27] …”

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: 92%

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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“…In contrast to SN4', S,N-heterotetracene system SN4'' comprising the heteroatom sequence 'SNNS' is built-up by annulation of two 'outer' thiophene and two 'inner' pyrrole rings resulting in the symmetric sequence of heteroatoms in the tetracyclic conjugated π-system. The multistep synthesis of Pr-SN4'' 33 started from 2-thienylcarbaldehyde (23), which was put to reaction with methyl 2-azidoactetate [46] Final removal of the TIPS-protecting group by TBAF gave the novel SN4''-system 33 in 98% yield (Scheme 6).…”

Section: Synthesis Of Sn-heterotetracenes Sn4''mentioning

confidence: 99%

“…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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Dual‐Strategy Tailoring Molecular Structures of Dopant‐Free Hole Transport Materials for Efficient and Stable Perovskite Solar Cells

Xie,

Wang,

Yin

et al. 2024

Angewandte Chemie

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Dopant‐free hole transport materials (HTMs) are ideal materials for highly efficient and stable n‐i‐p perovskite solar cells (PSCs), but most current design strategies for tailoring the molecular structures of HTMs are limited to single strategy. Herein, four HTMs based on dithienothiophenepyrrole (DTTP) core are devised through dual‐strategy methods combining conjugate engineering and side chain engineering. DTTP‐ThSO with ester alkyl chain that can form six‐membered ring by the S···O noncovalent conformation lock with thiophene in the backbone shows good planarity, high‐quality film, matching energy level and high hole mobility, as well as strong defect passivation ability. Consequently, a remarkable power conversion efficiency (PCE) of 23.3% with a nice long‐term stability is achieved by dopant‐free DTTP‐ThSO‐based PSCs, representing one of the highest values for un‐doped organic HTMs based PSCs. Especially, the fill factor (FF) of 82.3% is the highest value for dopant‐free small molecular HTMs‐based n‐i‐p PSCs to date. Moreover, DTTP‐ThSO‐based devices have achieved an excellent PCE of 20.9% in large‐area (1.01 cm2) devices. This work clearly elucidates the structure‐performance relationships of HTMs and offers a practical dual‐strategy approach to designing dopant‐free HTMs for high‐performance PSCs.

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Dimesitylboron Endcapped S,N-Heteroacenes: Syntheses, Photophysical and Fluoride-binding Properties

Cited by 4 publications

References 21 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

Synthesis and characterization of S,N-heterotetracenes

Dual‐Strategy Tailoring Molecular Structures of Dopant‐Free Hole Transport Materials for Efficient and Stable Perovskite Solar Cells

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