NIR electrochemical fluorescence switching from polymethine dyes

A polymethine dye was used as a fluorophore and an electroactive modulator in order to achieve reversible electrochemical fluorescence switching in the near infrared (NIR) region. An NIR emissive polymethine dye, 3 H -indolium, 2-[2-[2-chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(phenylmethyl)-2 H -indo...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2014-01, Vol.5 (4), p.1538-1544
Main Authors: Seo, Seogjae, Pascal, Simon, Park, Chihyun, Shin, Kyoungsoon, Yang, Xu, Maury, Olivier, Sarwade, Bhimrao D., Andraud, Chantal, Kim, Eunkyoung
Format: Article
Language:English
Subjects:
Chemical compounds
Chemical reactions
Chemical Sciences
Dyes
Fluorescence
Infrared
Inorganic chemistry
Material chemistry
Modulators
Organic chemistry
Switching
Wire
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Summary:A polymethine dye was used as a fluorophore and an electroactive modulator in order to achieve reversible electrochemical fluorescence switching in the near infrared (NIR) region. An NIR emissive polymethine dye, 3 H -indolium, 2-[2-[2-chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(phenylmethyl)-2 H -indol-2-ylidene]ethylidene]-5-(1,1-dimethylethyl)-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-(phenylmethyl)-bromide (PM1), displayed high absorption and emission in the NIR region. In addition, it showed a relatively reversible electrochemical reaction between −0.5 and 1.1 V vs. Ag wire. In contrast, a keto group (CO) bridged polymethine analogue, 2,6-bis[2-(1,3-dihydro-1-hexyl-3,3-dimethyl-2 H -indol-2-ylidene)ethylidene]-4-(1,1-dimethylethyl)cyclohexanone (PM2), showed an irreversible electrochemical reaction, possibly due to the keto group interrupting the full conjugation of the entire molecule in PM2. The reversible redox reaction of PM1 allowed electrochemical fluorescence switching in the NIR region for the first time. The NIR fluorescence switching was visually observable through a visible light cut-off filter with a cyclability of over 100.
ISSN:2041-6520
2041-6539
DOI:10.1039/C3SC53161A