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Osaki H, Chou CM, Taki M, et al. A Macrocyclic Fluorophore Dimer with Flexible Linkers: Bright Excimer Emission with a Long Fluorescence Lifetime. Angew Chem Int Ed Engl. 2016;55(25):7131-5doi: 10.1002/anie.201602239.
Osaki, H., Chou, C. M., Taki, M., Welke, K., Yokogawa, D., Irle, S., Sato, Y., Higashiyama, T., Saito, S., Fukazawa, A., & Yamaguchi, S. (2016). A Macrocyclic Fluorophore Dimer with Flexible Linkers: Bright Excimer Emission with a Long Fluorescence Lifetime. Angewandte Chemie (International ed. in English), 55(25), 7131-5. https://doi.org/10.1002/anie.201602239
Osaki, Hiroshi, et al. "A Macrocyclic Fluorophore Dimer with Flexible Linkers: Bright Excimer Emission with a Long Fluorescence Lifetime." Angewandte Chemie (International ed. in English) vol. 55,25 (2016): 7131-5. doi: https://doi.org/10.1002/anie.201602239
Osaki H, Chou CM, Taki M, Welke K, Yokogawa D, Irle S, Sato Y, Higashiyama T, Saito S, Fukazawa A, Yamaguchi S. A Macrocyclic Fluorophore Dimer with Flexible Linkers: Bright Excimer Emission with a Long Fluorescence Lifetime. Angew Chem Int Ed Engl. 2016 Jun 13;55(25):7131-5. doi: 10.1002/anie.201602239. Epub 2016 Apr 28. PMID: 27121201.
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Angew Chem Int Ed Engl. 2016 Jun 13;55(25):7131-5. doi: 10.1002/anie.201602239. Epub 2016 Apr 28.

A Macrocyclic Fluorophore Dimer with Flexible Linkers: Bright Excimer Emission with a Long Fluorescence Lifetime.

Angewandte Chemie (International ed. in English)

Hiroshi Osaki, Chih-Ming Chou, Masayasu Taki, Kai Welke, Daisuke Yokogawa, Stephan Irle, Yoshikatsu Sato, Tetsuya Higashiyama, Shohei Saito, Aiko Fukazawa, Shigehiro Yamaguchi

Affiliations

  1. Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan.
  2. Department of Applied Chemistry, National University of Kaohsiung, 700 Kaohsiung University Road, Kaohsiung, 811, Taiwan.
  3. Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan. [email protected].
  4. Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan.
  5. Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan. [email protected].
  6. Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan. [email protected].
  7. Division of Biological Science, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan.
  8. Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan. [email protected].
  9. Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo, Chikusa, Nagoya, 464-8602, Japan. [email protected].

PMID: 27121201 DOI: 10.1002/anie.201602239

Abstract

Bright fluorescent molecules with long fluorescence lifetimes are important for the development of lifetime-based fluorescence imaging techniques. Herein, a molecular design is described for simultaneously attaining long fluorescence lifetime (τ) and high brightness (ΦF ×ɛ) in a system that features macrocyclic dimerization of fluorescent π-conjugated skeletons with flexible linkers. An alkylene-linked macrocyclic dimer of bis(thienylethynyl)anthracene was found to show excimer emission with a long fluorescence lifetime (τ≈19 ns) in solution, while maintaining high brightness. A comparison with various relevant derivatives revealed that the macrocyclic structure and the length of the alkylene chains play crucial roles in attaining these properties. In vitro time-gated imaging experiments were conducted as a proof-of-principle for the superiority of this macrocyclic fluorophore relative to the commercial fluorescent dye Alexa Fluor 488.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: excimer; fluorescence; imaging agents; photophysics; pi conjugation

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