1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

29 December 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

Ynamide
anthracene
Tetracyanobutadiene
Luminescence
DFT

Supplementary materials

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