Synthesis and Physical Study of Perylene and Anthracene Polynitrile as Electron Acceptors

Li, Tingyu; Lin, Yi‐Chun; Song, Yu-Huei; Lu, Hsiu‐Feng; Chao, Ito; Lin, Chih‐Hsiu

doi:10.1021/acs.orglett.9b01454

Cited by 3 publications

(2 citation statements)

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“…171 Lin et al used the borylation of anthraquinone and subsequent oxidation to install the desired alkoxy substituents in their synthesis of highly electron-deficient perylene polynitriles (Scheme 98). 172 Perylenediimides (PDIs) are valuable chromophores for applications in dye chemistry and organic materials. Traditionally, elaboration of the perylenediimide core has been achieved by halogenation and subsequent downstream functionalization of the 1, 6, 7, and 12 "bay positions," which tend to twist the ring out of planarity.…”

Section: Transition-metal-catalyzed Borylation Of Aryl C−h Bonds For ...mentioning

confidence: 99%

Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules

Yu,

Wilson,

Hartwig

2023

Chem. Rev.

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The functionalization of C−H bonds in organic molecules containing functional groups has been one of the holy grails of catalysis. One synthetically important approach to the diverse functionalization of C−H bonds is the catalytic silylation or borylation of C−H bonds, which enables a broad array of downstream transformations to afford diverse structures. Advances in both undirected and directed methods for the transition-metal-catalyzed silylation and borylation of C−H bonds have led to their rapid adoption in early-, mid-, and late-stage of the synthesis of complex molecules. In this Review, we review the application of the transition-metal-catalyzed silylation and borylation of C−H bonds to the synthesis of bioactive molecules, organic materials, and ligands. Overall, we aim to provide a picture of the state of art of the silylation and borylation of C−H bonds as applied to the synthesis and modification of diverse architectures that will spur further application and development of these reactions.

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Section: Transition-metal-catalyzed Borylation Of Aryl C−h Bonds For ...mentioning

confidence: 99%

Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules

Yu,

Wilson,

Hartwig

2023

Chem. Rev.

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“…The key synthetic reactions used in this report are the Wittig–Knoevenagel benzannulation and nucleophilic addition/oxidation cyanation (Scheme a,b). In the benzannulation reaction, the maleimide first undergoes Michael addition with trialkyl phosphine to generate a Wittig reagent which reacts with an ortho-keto aryl aldehyde.…”

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confidence: 99%

Tuning the LUMO Levels of Z-Shaped Perylene Diimide via Stepwise Cyanation

Billa

Lin

2021

J. Org. Chem.

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The central dogma in constructing organic electron acceptors is to attach electron-withdrawing groups to polycyclic aromatic hydrocarbons. Yet, the full potentials of many organic acceptors were never realized due to synthetic obstacles. By combining the Wittig−Knoevenagel benzannulation, the Pd(0)catalyzed cyanation, and nucleophilic addition/oxidation cyanation, six polynitrile Z-shaped perylene diimide were synthesized. These stable and soluble electron acceptors possess LUMO energy levels comparable with those of benchmark compounds. Electrochemical investigation reveals that each additional nitrile group reduces the LUMO energy by 0.2 eV.

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Rational design and crystal structure prediction of ring-fused double-PDI compounds as n-channel organic semiconductors: a DFT study

Debata

Sahoo

Khatua

et al. 2021

Phys. Chem. Chem. Phys.

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Synthesis and Physical Study of Perylene and Anthracene Polynitrile as Electron Acceptors

Cited by 3 publications

References 46 publications

Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules

Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules

Tuning the LUMO Levels of Z-Shaped Perylene Diimide via Stepwise Cyanation

Rational design and crystal structure prediction of ring-fused double-PDI compounds as n-channel organic semiconductors: a DFT study

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