Efficient End-Capping Synthesis of Neutral Donor-Acceptor [2]Rotaxanes Under Additive-Free and Mild Conditions

2014 ◽  
Vol 20 (48) ◽  
pp. 15998-16005 ◽  
Author(s):  
Yuya Domoto ◽  
Shohei Sase ◽  
Kei Goto
Keyword(s):  
Neutral Donor ◽  
Mild Conditions ◽  
Donor Acceptor ◽  
End Capping

End-Capping Effect of Quinoxalino[2,3-b′]porphyrin on Donor–Acceptor Copolymer and Improved Performance of Polymer Solar Cells

2016 ◽  
Vol 49 (10) ◽  
pp. 3723-3732 ◽  
Author(s):  
Liwei Wang ◽  
Zi Qiao ◽  
Chen Gao ◽  
Junwen Liu ◽  
Zhi-Guo Zhang ◽  
...  
Keyword(s):  
Solar Cells ◽  
Polymer Solar Cells ◽  
Donor Acceptor ◽  
Improved Performance ◽  
End Capping

scholarly journals Overcoming Back Electron Transfer Facilitates the Implementation of Electron Donor-Acceptor Complexes in Catalysis

2020 ◽  
Author(s):  
Edward McClain ◽  
Timothy Monos ◽  
Mayuko Mori ◽  
Joel Beatty ◽  
Corey Stephenson
Keyword(s):  
Electron Transfer ◽  
Electron Donor ◽  
Mild Conditions ◽  
Back Electron Transfer ◽  
Synthetic Utility ◽  
Visible Light Driven ◽  
Donor Acceptor ◽  
Alkylation Reactions ◽  
Donor Species ◽  
Ethyl Isonicotinate

Electron donor-acceptor (EDA) complexes can controllably generate radicals under mild conditions through selective photoexcitation events. However, unproductive reactivity from fast deactivation of the photoexcited complexes through back electron transfer has slowed the development of EDA complexes in synthetic methodology. Here, we disclose the study of EDA complexes derived from 2-methoxynaphthalene donor and acylated ethyl isonicotinate <i>N</i>-oxide acceptor that undergo a fast N–O bond fragmentation event upon photoexcitation. This reaction design not only overcomes the limitations of back electron transfer but also enables the regeneration of the donor species, representing a rare example EDA photochemistry in a catalytic regime. The synthetic utility is demonstrated through visible light-driven radical trifluoromethylation and Minisci alkylation reactions. The scalability of the EDA complex promoted reaction evidenced by the successful multigram-scale trifluoromethylation of methyl N-Boc pyrrole-2-carboxylate in a continuous flow manifold.

scholarly journals Halogen-bonding-promoted Photo-induced C–X Borylation of Aryl Halide using Phenol Derivatives

2022 ◽  
Author(s):  
Kazuki Matsuo ◽  
Eiji Yamaguchi ◽  
Akichika Itoh
Keyword(s):  
Functional Group ◽  
Aryl Halide ◽  
Halogen Bonding ◽  
Mechanistic Studies ◽  
Boronate Esters ◽  
Aryl Radicals ◽  
Phenol Derivatives ◽  
Mild Conditions ◽  
Donor Acceptor ◽  
Photo Induced Electron Transfer

This study investigates the photo-induced C–X borylation reaction of aryl halides by forming a halogen-bonding complex. The method employs 2-naphthol as a halogen-bonding acceptor and proceeds under mild conditions without a photoredox catalyst under 420 nm blue light irradiation. The method is highly chemoselective, broadly functional group tolerant, and provides concise access to corresponding boronate esters. Mechanistic studies reveal that forming the halogen-bonding complex between aryl halide and naphthol acts as an electron donor-acceptor complex to furnish aryl radicals through photo-induced electron transfer.

End Capping Does Matter: Enhanced Order and Charge Transport in Conjugated Donor–Acceptor Polymers

2015 ◽  
Vol 48 (18) ◽  
pp. 6369-6377 ◽  
Author(s):  
Unsal Koldemir ◽  
Sreenivasa Reddy Puniredd ◽  
Manfred Wagner ◽  
Sefaattin Tongay ◽  
Tracy D. McCarley ◽  
...  
Keyword(s):  
Charge Transport ◽  
Donor Acceptor ◽  
End Capping

scholarly journals Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells

Molecules ◽  
2020 ◽  
Vol 25 (20) ◽  
pp. 4700
Author(s):  
Thu Trang Do ◽  
Meera Stephen ◽  
Khai Leok Chan ◽  
Sergei Manzhos ◽  
Paul L. Burn ◽  
...  
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Bulk Heterojunction ◽  
High Thermal Stability ◽  
Electron Affinities ◽  
New Materials ◽  
Good Solubility ◽  
Wide Range ◽  
Donor Acceptor ◽  
End Capping

We introduce two novel solution-processable electron acceptors based on an isomeric core of the much explored diketopyrrolopyrrole (DPP) moiety, namely pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP). The newly designed and synthesized compounds, 6,6′-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione] (NAI-IsoDPP-NAI) and 5,5′-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)isoindoline-1,3-dione] (PI-IsoDPP-PI) have been synthesized via Suzuki couplings using IsoDPP as a central building block and napthalimide or phthalimide as end-capping groups. The materials both exhibit good solubility in a wide range of organic solvents including chloroform (CF), dichloromethane (DCM), and tetrahydrofuran (THF), and have a high thermal stability. The new materials absorb in the wavelength range of 300–600 nm and both compounds have similar electron affinities, with the electron affinities that are compatible with their use as acceptors in donor-acceptor bulk heterojunction (BHJ) organic solar cells. BHJ devices comprising the NAI-IsoDPP-NAI acceptor with poly(3-n-hexylthiophene) (P3HT) as the donor were found to have a better performance than the PI-IsoDPP-PI containing cells, with the best device having a VOC of 0.92 V, a JSC of 1.7 mAcm−2, a FF of 63%, and a PCE of 0.97%.

Construction of an Artificial Ferrimagnetic Lattice by Lithium Ion Insertion into a Neutral Donor/Acceptor Metal-Organic Framework

2016 ◽  
Vol 128 (17) ◽  
pp. 5324-5328 ◽  
Author(s):  
Kouji Taniguchi ◽  
Keisuke Narushima ◽  
Julien Mahin ◽  
Wataru Kosaka ◽  
Hitoshi Miyasaka
Keyword(s):  
Metal Organic Framework ◽  
Lithium Ion ◽  
Neutral Donor ◽  
Donor Acceptor ◽  
Metal Organic ◽  
Organic Framework ◽  
Ion Insertion

scholarly journals Development of highly efficient platinum catalysts for hydroalkoxylation and hydroamination of unactivated alkenes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yali Zhou ◽  
Xingjun Xu ◽  
Hongwei Sun ◽  
Guanyu Tao ◽  
Xiao-Yong Chang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Rational Design ◽  
Platinum Catalysts ◽  
High Reactivity ◽  
Structural Components ◽  
Mechanistic Studies ◽  
Mild Conditions ◽  
Naturally Occurring ◽  
Donor Acceptor ◽  
Type Intermediate

AbstractHydrofunctionalization, the direct addition of an X–H (e.g., X=O, N) bond across an alkene, is a desirable strategy to make heterocycles that are important structural components of naturally occurring molecules. Described here is the design and discovery of “donor–acceptor”-type platinum catalysts that are highly effective in both hydroalkoxylation and hydroamination of unactivated alkenes over a broad range of substrates under mild conditions. A number of alkene substitution patterns are accommodated, including tri-substituted, 1,1-disubstituted, (E)-disubstituted, (Z)-disubstituted and even mono-substituted double bonds. Detailed mechanistic investigations suggest a plausible pathway that includes an unexpected dissociation/re-association of the electron-deficient ligand to form an alkene-bound “donor–acceptor”-type intermediate. These mechanistic studies help understand the origins of the high reactivity exhibited by the catalytic system, and provide a foundation for the rational design of chiral catalysts towards asymmetric hydrofunctionalization reactions.

scholarly journals Overcoming Back Electron Transfer Facilitates the Implementation of Electron Donor-Acceptor Complexes in Catalysis

2020 ◽  
Author(s):  
Edward McClain ◽  
Timothy Monos ◽  
Mayuko Mori ◽  
Joel Beatty ◽  
Corey Stephenson
Keyword(s):  
Electron Transfer ◽  
Electron Donor ◽  
Mild Conditions ◽  
Back Electron Transfer ◽  
Synthetic Utility ◽  
Visible Light Driven ◽  
Donor Acceptor ◽  
Alkylation Reactions ◽  
Donor Species ◽  
Ethyl Isonicotinate

Electron donor-acceptor (EDA) complexes can controllably generate radicals under mild conditions through selective photoexcitation events. However, unproductive reactivity from fast deactivation of the photoexcited complexes through back electron transfer has slowed the development of EDA complexes in synthetic methodology. Here, we disclose the study of EDA complexes derived from 2-methoxynaphthalene donor and acylated ethyl isonicotinate <i>N</i>-oxide acceptor that undergo a fast N–O bond fragmentation event upon photoexcitation. This reaction design not only overcomes the limitations of back electron transfer but also enables the regeneration of the donor species, representing a rare example EDA photochemistry in a catalytic regime. The synthetic utility is demonstrated through visible light-driven radical trifluoromethylation and Minisci alkylation reactions. The scalability of the EDA complex promoted reaction evidenced by the successful multigram-scale trifluoromethylation of methyl N-Boc pyrrole-2-carboxylate in a continuous flow manifold.

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