ArticleOrganic letters2021
1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes.
Article in Organic letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 37 citations in OpenAlex.
- Substrate-Controlled Divergent Reactivity of 2-Alkynylindoles: [2 + 2] Cycloaddition-Retroelectrocyclization versus Tricyanovinylation for the Synthesis of NLOphores.The Journal of organic chemistry · 2026Article
- Controlling cyclodextrin host-guest complexation in water with dynamic pericyclic chemistry.Communications chemistry · 2025Article
- Synthesis and Optical Characterization of Hydrazone-Substituted Push-Pull-Type NLOphores.The Journal of organic chemistry · 2024Article
- Easy but Efficient: Facile Approach to Molecule with Theoretically Justified Donor-Acceptor Structure for Effective Photothermal Conversion and Intravenous Photothermal Therapy.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 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
- On the Mechanism of the Formal [2+2] Cycloaddition - Retro-electrocyclization (CA-RE) Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Nonlinear Optical and Ion Sensor Properties of Novel Molecules Conjugated by Click Chemistry.Polymers · 2022Article
- 3-Alkynylindoles as Building Blocks for the Synthesis of Electronically Tunable Indole-Based Push-Pull Chromophores.The Journal of organic chemistry · 2022Article
- 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
- 1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes.Organic letters · 2021Article
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Authors and funding
10 authors at 3 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2 + 2] or a [4 + 2] Diels-Alder process. DFT calculations unraveled the mechanism of the [2 + 2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR and far-red/near-IR photoluminescence in the solid state up to 1550 nm.
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