Efficient Synthesis of Trimethylsilyl-Substituted Dithieno[2,3-<i>b</i>:3′,2′-<i>d</i>]thiophene, Tetra[2,3-thienylene] and Hexa[2,3-thienylene] from Substituted [3,3′]Bithiophenyl

Wang, Yangguang; Wang, Zhihua; Zhao, Dongfeng; Wang, Zhen; Cheng, Yangxiang; Hua, Weiming

doi:10.1055/s-2007-985582

Cited by 15 publications

(6 citation statements)

References 5 publications

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“…1 and 2. In general, COTh and COTh-tetramethylsilane (TMS) and COTh-Ph were synthesized according to literature methods 46,47 . COTh-Py was synthesized by using a S N2 reaction of 1 and pyridine at room temperature that gave a yield of 57%.…”

Section: Resultsmentioning

confidence: 99%

“…To gain insight into the details of the AIE phenomenon of COTh and its derivatives, we analyzed their crystal structures (Supplementary Figs. 17−19) 46,47 . COTh and its derivatives examined all showed non-coplanar and saddle-type conformations, which avoid strong intermolecular π–π interactions that are detrimental for the luminescence to take place 12 .…”

Section: Resultsmentioning

confidence: 99%

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Non-aromatic annulene-based aggregation-induced emission system via aromaticity reversal process

Zhao¹,

Zheng

et al. 2019

Nat Commun

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141

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Aggregation-induced emission (AIE) is a photophysical phenomenon correlated closely with the excited-state intramolecular motions. Although AIE has attracted increasing attention due to the significant applications in biomedical and optoelectronics, an in-depth understanding of the excited-state intramolecular motion has yet to be fully developed. Here we found the non-aromatic annulene derivative of cyclooctatetrathiophene shows typical AIE phenomenon in spite of its rotor-free structure. The underlying mechanism is investigated through photoluminescence spectra, time-resolved absorption spectra, theoretical calculations, circular dichroism as well as by pressure-dependent fluorescent spectra etc., which indicate that the aromaticity reversal from ground state to the excited state serves as a driving force for inducing the excited-state intramolecular vibration, leading to the AIE phenomenon. Therefore, aromaticity reversal is demonstrated as a reliable strategy to develop vibrational AIE systems. This work also provides a new viewpoint to understand the excited-state intramolecular motion behavior of lumiongens.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Non-aromatic annulene-based aggregation-induced emission system via aromaticity reversal process

Zhao¹,

Zheng

et al. 2019

Nat Commun

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141

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“…The chemical structures of the PM6 donor, L15 acceptor, and three DTT volatile isomeric additives are displayed in Figure 1a, and the synthetic procedures and gel permeation chromatography (GPC) curve of L15 polymer acceptor (Figure S1, Supporting Information) are included in the Supporting Information. [32,33] As presented in Figure 1b, the highest occupied molecular orbital (HOMO) energy levels of three isomeric solid additives exhibit a gradual increase from −5.84 eV for DTT-1 to −5.70 eV for DTT-2 and −5.61 eV for DTT-3, while the lowest unoccupied molecular orbital (LUMO) levels show a decreasing trend from −0.57 to −0.75 and −1.10 eV, respectively. [34,35] The alterations of the energy levels can result in a narrower bandgap, indicating that the position isomerization of S atoms in DTT systems can enhance conjugation.…”

Section: Molecular Structure Theoretical Calculations and Volatilitymentioning

confidence: 99%

Isomerized Green Solid Additive Engineering for Thermally Stable and Eco‐Friendly All‐Polymer Solar Cells with Approaching 19% Efficiency

Liu,

Xu,

et al. 2023

Advanced Materials

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Laboratory‐scale all‐polymer solar cells (all‐PSCs) have exhibited remarkable power conversion efficiencies (PCEs) exceeding 19%. However, the utilization of hazardous solvents and nonvolatile liquid additives poses challenges for eco‐friendly commercialization, necessitating the trade‐off between device efficiency and operation stability. Herein, we propose an innovative approach based on isomerized solid additive engineering, employing volatile dithienothiophene (DTT) isomers to modulate intermolecular interactions and facilitate molecular stacking within the photoactive layers. Through elucidating the underlying principles of the DTT‐induced polymer assembly on a molecular level, we achieve a PCE of 18.72% for devices processed with environmentally benign solvents, ranking it among the highest record values for eco‐friendly all‐PSCs. Significantly, such superiorities of the DTT‐isomerized strategy afford excellent compatibility with large‐area blade‐coating techniques, offering a promising pathway for industrial‐scale manufacturing of PSCs. Moreover, these devices demonstrate enhanced thermal stability with a promising extrapolated T80 lifetime of 14000 h, further bolstering their potential for sustainable technological advancements.This article is protected by copyright. All rights reserved

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“…The compound BTBT was prepared according to our previous research work. 15 The concentration of n -BuLi (in hexane) was determined by titration with N -pivaloyl- o -toluidine. 16 Silica gel (300–400 mesh) was employed for column chromatography.…”

Section: Experimental Sectionmentioning

confidence: 99%

All-Thiophene-Based Double Helix: Synthesis, Crystal Structure, Chiroptical Property and Arylation

Zhang

et al. 2018

ACS Omega

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The all-thiophene-based double helix DH-1 was designed and prepared originally from the selective deprotonation of cyclooctatetrathiophene (tetra[3,4]thienylene, COTh ) and following the Negishi coupling reaction with 3,3′-bithiophene. The X-ray crystallographic studies revealed that DH-1 has a double-helical scaffold. The arylations including tetraphenylation and tetrathienylation were efficiently employed to replace the four α-protons of the central COTh of DH-1 with phenyl and thiophenyl groups via cross-coupling reactions. The chiral resolution of rac - DH-1 was fulfilled via chiral high-performance liquid chromatography, and the chiroptical properties were characterized by circular dichroism spectra and optical rotation. Ultraviolet–visible absorption and fluorescence behaviors of DH-1 and its arylation products were also characterized to describe the extended conjugated scaffold.

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Efficient Synthesis of Trimethylsilyl-Substituted Dithieno[2,3-b:3′,2′-d]thiophene, Tetra[2,3-thienylene] and Hexa[2,3-thienylene] from Substituted [3,3′]Bithiophenyl

Cited by 15 publications

References 5 publications

Non-aromatic annulene-based aggregation-induced emission system via aromaticity reversal process

Non-aromatic annulene-based aggregation-induced emission system via aromaticity reversal process

Isomerized Green Solid Additive Engineering for Thermally Stable and Eco‐Friendly All‐Polymer Solar Cells with Approaching 19% Efficiency

All-Thiophene-Based Double Helix: Synthesis, Crystal Structure, Chiroptical Property and Arylation

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