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?-extended anthracenes as sensitive probes for mechanical stress.

ABSTRACT: Smart molecular systems having the ability to report on mechanical strain or failure in polymers via alteration of their optical properties are of great interest in materials science. However, only limited attention has been devoted to targeted chromophore engineering to fine-tune their physicochemical properties. Here, we describe the synthesis of ?-extended anthracenes that can be released from their respective maleimide Diels-Alder adducts through the application of mechanical stress in solution and in the solid state. We demonstrate the improvement of fluorescence quantum yield as well as the tuning of excitation and emission wavelengths while retaining their excellent mechanochemical properties laying the foundation for a new series of mechanophores whose spectral characteristics can be modularly adjusted.

SUBMITTER: Gostl R

PROVIDER: S-EPMC5518546 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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π-extended anthracenes as sensitive probes for mechanical stress.

Göstl R R Sijbesma R P RP

Chemical science 20151007 1

Smart molecular systems having the ability to report on mechanical strain or failure in polymers <i>via</i> alteration of their optical properties are of great interest in materials science. However, only limited attention has been devoted to targeted chromophore engineering to fine-tune their physicochemical properties. Here, we describe the synthesis of π-extended anthracenes that can be released from their respective maleimide Diels-Alder adducts through the application of mechanical stress i ...[more]

PMID: 28791098

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