Dithienophosphole-based molecular electron acceptors constructed using direct (hetero)arylation cross-coupling methods

2018 ◽  
Vol 6 (8) ◽  
pp. 2148-2154 ◽  
Author(s):  
Thomas A. Welsh ◽  
Audrey Laventure ◽  
Thomas Baumgartner ◽  
Gregory C. Welch
Keyword(s):  
Building Block ◽  
Cross Coupling ◽  
Electron Acceptors ◽  
Bond Functionalization ◽  
Coupling Methods ◽  
Molecular Electron ◽  
End Caps

Herein we report on the first successful coupling of the dithienophosphole (S2PO) functional building block with three types of heteroaryl end caps using direct (hetero)arylation C–H bond functionalization methods.

An efficient method for the synthesis of 2-pyridones via C–H bond functionalization

2020 ◽  
Vol 56 (95) ◽  
pp. 15020-15023
Author(s):  
Shuguang Zhou ◽  
Duan-Yang Liu ◽  
Suo Wang ◽  
Jie-Sheng Tian ◽  
Teck-Peng Loh
Keyword(s):  
Efficient Method ◽  
Cross Coupling ◽  
Bond Functionalization ◽  
Plausible Mechanism

N-Substituted 2-pyridones are installed through the RhIII-catalyzed formal [3+3] annulation of enaminones with acrylates. Control and deuterated experiments led to a plausible mechanism involving C(sp2)–H bond cross-coupling and aminolysis cyclization.

Molecular electron acceptors for efficient fullerene-free organic solar cells

2017 ◽  
Vol 19 (5) ◽  
pp. 3440-3458 ◽  
Author(s):  
Shuixing Li ◽  
Zhongqiang Zhang ◽  
Minmin Shi ◽  
Chang-Zhi Li ◽  
Hongzheng Chen
Keyword(s):  
Solar Cells ◽  
Small Molecule ◽  
Organic Solar Cells ◽  
Wide Bandgap ◽  
Electron Acceptors ◽  
Electron Donors ◽  
Molecular Electron ◽  
Narrow Bandgap

Small molecule electron acceptors pairing with wide bandgap or narrow bandgap electron donors are reviewed and discussed for fullerene-free organic solar cells.

Synthesis and properties of azulene-functionalized BODIPYs

RSC Advances ◽  
2016 ◽  
Vol 6 (38) ◽  
pp. 32124-32129 ◽  
Author(s):  
Lizhi Gai ◽  
Jingzhi Chen ◽  
Yue Zhao ◽  
John Mack ◽  
Hua Lu ◽  
...  
Keyword(s):  
Building Block ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Small Series ◽  
Cross Coupling Reaction

A small series of BODIPY derivatives incorporating azulene were synthesized via Suzuki–Miyaura cross-coupling reaction. There has better conjugation through 2-position as building block.

Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 2009-2018
Author(s):  
Jan-Hendrik Lamm ◽  
Philipp Niermeier ◽  
Leif Körte ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Building Block ◽  
High Resolution Mass Spectrometry ◽  
Cross Coupling ◽  
Easy Access ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Resolution Mass

An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9H)-one was reacted with ethynylmagnesium bromide in the presence of CeCl3; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.

Fusion or non-fusion of quasi-two-dimensional fused perylene diimide acceptors: the importance of molecular geometry for fullerene-free organic solar cells

2019 ◽  
Vol 7 (48) ◽  
pp. 27493-27502 ◽  
Author(s):  
Yuli Yin ◽  
Zhi Zheng ◽  
Daoyuan Chen ◽  
Ming Liu ◽  
Jianqi Zhang ◽  
...  
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Molecular Geometry ◽  
Electron Acceptors ◽  
Perylene Diimide ◽  
Two Dimensional ◽  
Molecular Electron ◽  
Insight Into

Two small molecular electron acceptors (BT–FPDI and fBT–FPDI) with quasi-2D FPDI units were designed and synthesized for efficient fullerene-free organic solar cells (OSCs), and provide a new insight into the regulation of the molecular geometry.

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