Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene

Masaru Tanioka, Shinichiro Kamino, Atsuya Muranaka, Yousuke Ooyama, Hiromi Ota, Yoshinao Shirasaki, Jun Horigome, Masashi Ueda, Masanobu Uchiyama, Daisuke Sawada, Shuichi Enomoto

Research output: Contribution to journalArticle

95 Citations (Scopus)

Abstract

Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX010, which shows switchable near-IR and blue fluorescence responses. Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion between the two molecular packing arrangements in response to mechanical grinding and solvent vapor-fuming.

Original languageEnglish
Pages (from-to)6436-6439
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number20
DOIs
Publication statusPublished - May 27 2015

Fingerprint

Fluorescence
Infrared radiation
Molecules
Structural dynamics
Monomers
Vapors
X-Rays
Single crystals
X rays
Wavelength
Crystals

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Tanioka, M., Kamino, S., Muranaka, A., Ooyama, Y., Ota, H., Shirasaki, Y., ... Enomoto, S. (2015). Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene. Journal of the American Chemical Society, 137(20), 6436-6439. https://doi.org/10.1021/jacs.5b00877

Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene. / Tanioka, Masaru; Kamino, Shinichiro; Muranaka, Atsuya; Ooyama, Yousuke; Ota, Hiromi; Shirasaki, Yoshinao; Horigome, Jun; Ueda, Masashi; Uchiyama, Masanobu; Sawada, Daisuke; Enomoto, Shuichi.

In: Journal of the American Chemical Society, Vol. 137, No. 20, 27.05.2015, p. 6436-6439.

Research output: Contribution to journalArticle

Tanioka, M, Kamino, S, Muranaka, A, Ooyama, Y, Ota, H, Shirasaki, Y, Horigome, J, Ueda, M, Uchiyama, M, Sawada, D & Enomoto, S 2015, 'Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene', Journal of the American Chemical Society, vol. 137, no. 20, pp. 6436-6439. https://doi.org/10.1021/jacs.5b00877
Tanioka M, Kamino S, Muranaka A, Ooyama Y, Ota H, Shirasaki Y et al. Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene. Journal of the American Chemical Society. 2015 May 27;137(20):6436-6439. https://doi.org/10.1021/jacs.5b00877
Tanioka, Masaru ; Kamino, Shinichiro ; Muranaka, Atsuya ; Ooyama, Yousuke ; Ota, Hiromi ; Shirasaki, Yoshinao ; Horigome, Jun ; Ueda, Masashi ; Uchiyama, Masanobu ; Sawada, Daisuke ; Enomoto, Shuichi. / Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 20. pp. 6436-6439.
@article{307b70477a0f493fb8ddf59e585c34ca,
title = "Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene",
abstract = "Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX010, which shows switchable near-IR and blue fluorescence responses. Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion between the two molecular packing arrangements in response to mechanical grinding and solvent vapor-fuming.",
author = "Masaru Tanioka and Shinichiro Kamino and Atsuya Muranaka and Yousuke Ooyama and Hiromi Ota and Yoshinao Shirasaki and Jun Horigome and Masashi Ueda and Masanobu Uchiyama and Daisuke Sawada and Shuichi Enomoto",
year = "2015",
month = "5",
day = "27",
doi = "10.1021/jacs.5b00877",
language = "English",
volume = "137",
pages = "6436--6439",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

T1 - Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene

AU - Tanioka, Masaru

AU - Kamino, Shinichiro

AU - Muranaka, Atsuya

AU - Ooyama, Yousuke

AU - Ota, Hiromi

AU - Shirasaki, Yoshinao

AU - Horigome, Jun

AU - Ueda, Masashi

AU - Uchiyama, Masanobu

AU - Sawada, Daisuke

AU - Enomoto, Shuichi

PY - 2015/5/27

Y1 - 2015/5/27

N2 - Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX010, which shows switchable near-IR and blue fluorescence responses. Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion between the two molecular packing arrangements in response to mechanical grinding and solvent vapor-fuming.

AB - Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX010, which shows switchable near-IR and blue fluorescence responses. Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion between the two molecular packing arrangements in response to mechanical grinding and solvent vapor-fuming.

UR - http://www.scopus.com/inward/record.url?scp=84930226963&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84930226963&partnerID=8YFLogxK

U2 - 10.1021/jacs.5b00877

DO - 10.1021/jacs.5b00877

M3 - Article

C2 - 25965882

AN - SCOPUS:84930226963

VL - 137

SP - 6436

EP - 6439

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 20

ER -