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Probing Force with Mechanobase‐Induced Chemiluminescence
Author(s) -
Clough Jess M.,
Balan Abidin,
van Daal Tom L. J.,
Sijbesma Rint P.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508840
Subject(s) - mechanoluminescence , chemiluminescence , chemistry , photochemistry , tetrahydrofuran , sonication , dioxetane , palladium , combinatorial chemistry , catalysis , luminescence , organic chemistry , materials science , chromatography , solvent , optoelectronics
Mechanophores capable of releasing N‐heterocyclic carbene (NHC), a strong base, are combined with triggerable chemiluminescent substrates to give a novel system for mechanically induced chemiluminescence. The mechanophores are palladium bis‐NHC complexes, centrally incorporated in poly(tetrahydrofuran) (pTHF). Chemiluminescence is induced from two substrates, adamantyl phenol dioxetane (APD) and a coumaranone derivative, upon sonication of dilute solutions of the polymer complex and either APD or the coumaranone. Control experiments with a low molecular weight Pd complex showed no significant activation and the molecular weight dependence of the coumaranone emission supports the mechanical origin of the activation. The development of this system is a first step towards mechanoluminescence at lower force thresholds and catalytic mechanoluminescence.