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Transformation of π-conjugated macrocycles: from furanophanes to napthalenophanes.


ABSTRACT: Applying sequential Diels-Alder cycloaddition and deoxygenation to small π-conjugated furan macrocycles fully converts them to 1,4-naphthalophanes with either ethylene or acetylene spacers, depending on the reaction conditions. 1,4-Napthalenophane tetraene exhibits a 1,3-alternating conformation in the solid state, inclusion of solvent molecules within the macrocycle, and low reduction potentials.

SUBMITTER: Rajagopal SK 

PROVIDER: S-EPMC9756652 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Transformation of π-conjugated macrocycles: from furanophanes to napthalenophanes.

Rajagopal Shinaj K SK   Dishi Or O   Bogoslavsky Benny B   Gidron Ori O  

Chemical communications (Cambridge, England) 20221208 98


Applying sequential Diels-Alder cycloaddition and deoxygenation to small π-conjugated furan macrocycles fully converts them to 1,4-naphthalophanes with either ethylene or acetylene spacers, depending on the reaction conditions. 1,4-Napthalenophane tetraene exhibits a 1,3-alternating conformation in the solid state, inclusion of solvent molecules within the macrocycle, and low reduction potentials. ...[more]

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