NIR Electrofluorochromic Properties of Aza-Boron-dipyrromethene Dyes

Hanwhuy Lim; Seogjae Seo; Simon Pascal; Quentin Bellier; Stéphane Rigaut; Chihyun Park; Haijin Shin; Olivier Maury; Chantal Andraud; Eunkyoung Kim

doi:10.1038/srep18867

NIR Electrofluorochromic Properties of Aza-Boron-dipyrromethene Dyes

Hanwhuy Lim, Seogjae Seo, Simon Pascal, Quentin Bellier, Stéphane Rigaut, Chihyun Park, Haijin Shin, Olivier Maury, Chantal Andraud, Eunkyoung Kim

Department of Chemical and Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

The photophysical properties of near-infrared (NIR) emissive aza-boron-dipyrromethene (aza-BDP) dyes incorporating nitrofluorene and alkoxy decorations were intensively investigated. Their highly reversible one-electron reduction process showed characteristic electrofluorochromic (EF) properties in the NIR range, depending on the substituents. The nitrofluorene ethynyl-substituted (Type I) dyes showed smaller EF effects than the alkoxy-containing (Type II) dyes because of the difference in their intrinsic fluorescence contrast between the neutral and reduced states (radical anion). In addition, the Type II chromophores showed a larger diffusion coefficient for ion transport, which enhanced the EF contrast and the response time for the fluorescence change at a given step potential. With an optimized condition, the NIR EF ON/OFF ratio reached a value of 6.1 and a long cyclability over 1000 EF cycles between -0.4V and +0.4V switching potentials, with approximately 20% loss of the initial ON/OFF switching ratio. The NIR EF switching was visually observed through a visible light cut-off filter, featuring high fluorescence contrast.

Original language	English
Article number	18867
Journal	Scientific reports
Volume	6
DOIs	https://doi.org/10.1038/srep18867
Publication status	Published - 2016 Jan 6

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (No. 2007-0056091). This research was supported by a grant of the Korea Health Technology R&D Project through the Korea Health Industry Development Institute (KHIDI), funded by the Ministry of Health & Welfare, Republic of Korea (grant number : HI15C0942).

Publisher Copyright:
© 2016, Macmillan Publishers Limited. All rights reserved.

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title = "NIR Electrofluorochromic Properties of Aza-Boron-dipyrromethene Dyes",

abstract = "The photophysical properties of near-infrared (NIR) emissive aza-boron-dipyrromethene (aza-BDP) dyes incorporating nitrofluorene and alkoxy decorations were intensively investigated. Their highly reversible one-electron reduction process showed characteristic electrofluorochromic (EF) properties in the NIR range, depending on the substituents. The nitrofluorene ethynyl-substituted (Type I) dyes showed smaller EF effects than the alkoxy-containing (Type II) dyes because of the difference in their intrinsic fluorescence contrast between the neutral and reduced states (radical anion). In addition, the Type II chromophores showed a larger diffusion coefficient for ion transport, which enhanced the EF contrast and the response time for the fluorescence change at a given step potential. With an optimized condition, the NIR EF ON/OFF ratio reached a value of 6.1 and a long cyclability over 1000 EF cycles between -0.4V and +0.4V switching potentials, with approximately 20% loss of the initial ON/OFF switching ratio. The NIR EF switching was visually observed through a visible light cut-off filter, featuring high fluorescence contrast.",

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note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (No. 2007-0056091). This research was supported by a grant of the Korea Health Technology R&D Project through the Korea Health Industry Development Institute (KHIDI), funded by the Ministry of Health & Welfare, Republic of Korea (grant number : HI15C0942). Publisher Copyright: {\textcopyright} 2016, Macmillan Publishers Limited. All rights reserved.",

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AU - Lim, Hanwhuy

AU - Seo, Seogjae

AU - Pascal, Simon

AU - Bellier, Quentin

AU - Rigaut, Stéphane

AU - Park, Chihyun

AU - Shin, Haijin

AU - Maury, Olivier

AU - Andraud, Chantal

AU - Kim, Eunkyoung

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (No. 2007-0056091). This research was supported by a grant of the Korea Health Technology R&D Project through the Korea Health Industry Development Institute (KHIDI), funded by the Ministry of Health & Welfare, Republic of Korea (grant number : HI15C0942). Publisher Copyright: © 2016, Macmillan Publishers Limited. All rights reserved.

PY - 2016/1/6

Y1 - 2016/1/6

N2 - The photophysical properties of near-infrared (NIR) emissive aza-boron-dipyrromethene (aza-BDP) dyes incorporating nitrofluorene and alkoxy decorations were intensively investigated. Their highly reversible one-electron reduction process showed characteristic electrofluorochromic (EF) properties in the NIR range, depending on the substituents. The nitrofluorene ethynyl-substituted (Type I) dyes showed smaller EF effects than the alkoxy-containing (Type II) dyes because of the difference in their intrinsic fluorescence contrast between the neutral and reduced states (radical anion). In addition, the Type II chromophores showed a larger diffusion coefficient for ion transport, which enhanced the EF contrast and the response time for the fluorescence change at a given step potential. With an optimized condition, the NIR EF ON/OFF ratio reached a value of 6.1 and a long cyclability over 1000 EF cycles between -0.4V and +0.4V switching potentials, with approximately 20% loss of the initial ON/OFF switching ratio. The NIR EF switching was visually observed through a visible light cut-off filter, featuring high fluorescence contrast.

AB - The photophysical properties of near-infrared (NIR) emissive aza-boron-dipyrromethene (aza-BDP) dyes incorporating nitrofluorene and alkoxy decorations were intensively investigated. Their highly reversible one-electron reduction process showed characteristic electrofluorochromic (EF) properties in the NIR range, depending on the substituents. The nitrofluorene ethynyl-substituted (Type I) dyes showed smaller EF effects than the alkoxy-containing (Type II) dyes because of the difference in their intrinsic fluorescence contrast between the neutral and reduced states (radical anion). In addition, the Type II chromophores showed a larger diffusion coefficient for ion transport, which enhanced the EF contrast and the response time for the fluorescence change at a given step potential. With an optimized condition, the NIR EF ON/OFF ratio reached a value of 6.1 and a long cyclability over 1000 EF cycles between -0.4V and +0.4V switching potentials, with approximately 20% loss of the initial ON/OFF switching ratio. The NIR EF switching was visually observed through a visible light cut-off filter, featuring high fluorescence contrast.

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NIR Electrofluorochromic Properties of Aza-Boron-dipyrromethene Dyes

Abstract

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