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Issue 24, 2011
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Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

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Abstract

The green-fluorescent protein of the jellyfish operates with the most powerful phenolate donors in the push–pull fluorophore. To nevertheless achieve red fluorescence with the same architecture, sea anemone and corals apply oxidative imination, a process that accounts for the chemistry of vision as well. The objective of this study was to apply these lessons from nature to one of the most compact family of panchromatic fluorophores, i.e. core-substituted naphthalenediimides (cNDIs). We report straightforward synthetic access to hydroxylated cNDI and cPDI cores by palladium-catalyzed cleavage of allyloxy substituents. With hydroxylated cNDIs but not cPDIs in water-containing media, excited-state intramolecular proton transfer yields a second bathochromic emission. Deprotonation of hydroquinone, catechol and boronic ester cores provides access to an impressive panchromism up to the NIR frontier at 640 nm. With cNDIs, oxidative imination gives red shifts up to 638 nm, whereas the expanded cPDIs already absorb at 754 nm upon deprotonation of hydroquinone cores. The practical usefulness of hydroquinone cNDIs is exemplified by ratiometric sensing of the purity of DMF with the “naked eye” at a sensitivity far beyond the “naked nose”. We conclude that the panchromatic hypersensitivity toward the environment of the new cNDIs is ideal for pattern generation in differential sensing arrays.

Graphical abstract: Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

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Supplementary files

Article information


Submitted
03 May 2011
Accepted
11 Jul 2011
First published
30 Aug 2011

Org. Biomol. Chem., 2011,9, 8246-8252
Article type
Paper

Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

A. Fin, I. Petkova, D. A. Doval, N. Sakai, E. Vauthey and S. Matile, Org. Biomol. Chem., 2011, 9, 8246
DOI: 10.1039/C1OB05702B

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