NIR electrochemical fluorescence switching from polymethine dyes

Seogjae Seo, Simon Pascal, Chihyun Park, Kyoungsoon Shin, Xu Yang, Olivier Maury, Bhimrao D. Sarwade, Chantal Andraud, Eunkyoung Kim

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

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, 3H-indolium, 2-[2-[2-chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(phenylmethyl) -2H-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 (CO) bridged polymethine analogue, 2,6-bis[2-(1,3-dihydro-1-hexyl-3,3- dimethyl-2H-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.

Original languageEnglish
Pages (from-to)1538-1544
Number of pages7
JournalChemical Science
Volume5
Issue number4
DOIs
Publication statusPublished - 2014 Apr 1

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Coloring Agents
Fluorescence
Infrared radiation
Fluorophores
Redox reactions
Carbon Monoxide
Bromides
Modulators
VPM chloride
Wire
Molecules

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Seo, S., Pascal, S., Park, C., Shin, K., Yang, X., Maury, O., ... Kim, E. (2014). NIR electrochemical fluorescence switching from polymethine dyes. Chemical Science, 5(4), 1538-1544. https://doi.org/10.1039/c3sc53161a
Seo, Seogjae ; Pascal, Simon ; Park, Chihyun ; Shin, Kyoungsoon ; Yang, Xu ; Maury, Olivier ; Sarwade, Bhimrao D. ; Andraud, Chantal ; Kim, Eunkyoung. / NIR electrochemical fluorescence switching from polymethine dyes. In: Chemical Science. 2014 ; Vol. 5, No. 4. pp. 1538-1544.
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abstract = "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, 3H-indolium, 2-[2-[2-chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(phenylmethyl) -2H-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 (CO) bridged polymethine analogue, 2,6-bis[2-(1,3-dihydro-1-hexyl-3,3- dimethyl-2H-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.",
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Seo, S, Pascal, S, Park, C, Shin, K, Yang, X, Maury, O, Sarwade, BD, Andraud, C & Kim, E 2014, 'NIR electrochemical fluorescence switching from polymethine dyes', Chemical Science, vol. 5, no. 4, pp. 1538-1544. https://doi.org/10.1039/c3sc53161a

NIR electrochemical fluorescence switching from polymethine dyes. / Seo, Seogjae; Pascal, Simon; Park, Chihyun; Shin, Kyoungsoon; Yang, Xu; Maury, Olivier; Sarwade, Bhimrao D.; Andraud, Chantal; Kim, Eunkyoung.

In: Chemical Science, Vol. 5, No. 4, 01.04.2014, p. 1538-1544.

Research output: Contribution to journalArticle

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AU - Seo, Seogjae

AU - Pascal, Simon

AU - Park, Chihyun

AU - Shin, Kyoungsoon

AU - Yang, Xu

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AU - Sarwade, Bhimrao D.

AU - Andraud, Chantal

AU - Kim, Eunkyoung

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N2 - 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, 3H-indolium, 2-[2-[2-chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(phenylmethyl) -2H-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 (CO) bridged polymethine analogue, 2,6-bis[2-(1,3-dihydro-1-hexyl-3,3- dimethyl-2H-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.

AB - 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, 3H-indolium, 2-[2-[2-chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(phenylmethyl) -2H-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 (CO) bridged polymethine analogue, 2,6-bis[2-(1,3-dihydro-1-hexyl-3,3- dimethyl-2H-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.

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Seo S, Pascal S, Park C, Shin K, Yang X, Maury O et al. NIR electrochemical fluorescence switching from polymethine dyes. Chemical Science. 2014 Apr 1;5(4):1538-1544. https://doi.org/10.1039/c3sc53161a