ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Expanding the Chemical Space of Tetracyanobuta-1,3-diene (TCBD) through a Cyano-Diels-Alder Reaction: Synthesis, Structure, and Physicochemical Properties of an Anthryl-fused-TCBD Derivative.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed.
- Azaporphyrinoid-Based Photo- and Electroactive Architectures for Advanced Functional Materials.Advanced materials (Deerfield Beach, Fla.) · 2026Review
- Unprecedented "off-pathway" [2+2] Cycloaddition-Retroelectrocyclization Reaction Between an Unsymmetric Alkyne and Tetracyanoquinodimethane.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis and Optical Characterization of Hydrazone-Substituted Push-Pull-Type NLOphores.The Journal of organic chemistry · 2024Article
- Perspectives on push-pull chromophores derived from click-type [2 + 2] cycloaddition-retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes.Beilstein journal of organic chemistry · 2024Review
- Minimalist Design for Solar Energy Conversion: Revamping the π-Grid of an Organic Framework into Open-Shell Superabsorbers.JACS Au · 2023Article
- Expanding the Chemical Space of Tetracyanobuta-1,3-diene (TCBD) through a Cyano-Diels-Alder Reaction: Synthesis, Structure, and Physicochemical Properties of an Anthryl-fused-TCBD Derivative.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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7 authors.
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Abstract
Tetracyanobuta-1,3-diene (TCBD) is a powerful and versatile electron-acceptor moiety widely used for the preparation of electroactive conjugates. While many reports addressing its electron-accepting capability have appeared in the literature, significantly scarcer are those dealing with its chemical modification, a relevant topic which allows to broaden the chemical space of this interesting functional unit. Here, we report on the first example of a high-yielding cyano-Diels-Alder (CDA) reaction between TCBD, that is, where a nitrile group acts as a dienophile, and an anthryl moiety, that is, acting as a diene. The resulting anthryl-fused-TCBD derivative, which structure was unambiguously identified by X-ray diffraction, shows high thermal stability, remarkable electron-accepting capability, and interesting electronic ground- and excited-state features, as characterized by a thorough theoretical, electrochemical, and photophysical investigation. Moreover, a detailed kinetic analysis of the intramolecular CDA reaction transforming the anthryl-TCBD-based reactant into the anthryl-fused-TCBD product was carried out at different temperatures.
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