Dual Emission and Mechanofluorochromism of a V-Shaped π-System Composed of Disulfonyl-Substituted Dibenzocyclooctatetraenes

Takanori Nishida; Shinya Ohta; Feng Xu; Kenta Shinohara; Takahiro Kamada; Haruo Akashi; Makoto Takezaki; Kan Wakamatsu; Akihiro Orita

doi:10.1021/acs.orglett.6b01786

Dual Emission and Mechanofluorochromism of a V-Shaped π-System Composed of Disulfonyl-Substituted Dibenzocyclooctatetraenes

Takanori Nishida
, Shinya Ohta
, Feng Xu
, Kenta Shinohara
, Takahiro Kamada
, Haruo Akashi
, Makoto Takezaki
, Kan Wakamatsu
, Akihiro Orita

Chemistry (Twin Cities)

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

13 Scopus citations

Abstract

A series of dibenzocyclooctatetraenes 6 bearing phenylethynyl and phenylsulfonyl groups were synthesized from bromo-substituted formylbenzyl sulfone 4 via cyclic dimerization of 4 and Sonogashira coupling of the resulting dibromocyclooctatetraene 3 with terminal acetylenes. The diamino derivative 6b exhibited dual emission with emission maxima at 436 and 547 nm. Furthermore, in the fluorescence of 6b, solvatofluorochromism was observed in response to solvent polarity, whereas in the solid states, mechanofluorochromism was observed.

Original language	English (US)
Pages (from-to)	3988-3991
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.6b01786
State	Published - Aug 19 2016

Bibliographical note

Funding Information:
This work was supported by JSPS KAKENHI Grants JP16H01164 in Middle Molecular Strategy and JP15K05440, the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects.

Publisher Copyright:
© 2016 American Chemical Society.

Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.

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10.1021/acs.orglett.6b01786

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title = "Dual Emission and Mechanofluorochromism of a V-Shaped π-System Composed of Disulfonyl-Substituted Dibenzocyclooctatetraenes",

abstract = "A series of dibenzocyclooctatetraenes 6 bearing phenylethynyl and phenylsulfonyl groups were synthesized from bromo-substituted formylbenzyl sulfone 4 via cyclic dimerization of 4 and Sonogashira coupling of the resulting dibromocyclooctatetraene 3 with terminal acetylenes. The diamino derivative 6b exhibited dual emission with emission maxima at 436 and 547 nm. Furthermore, in the fluorescence of 6b, solvatofluorochromism was observed in response to solvent polarity, whereas in the solid states, mechanofluorochromism was observed.",

author = "Takanori Nishida and Shinya Ohta and Feng Xu and Kenta Shinohara and Takahiro Kamada and Haruo Akashi and Makoto Takezaki and Kan Wakamatsu and Akihiro Orita",

note = "Funding Information: This work was supported by JSPS KAKENHI Grants JP16H01164 in Middle Molecular Strategy and JP15K05440, the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. Publisher Copyright: {\textcopyright} 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

year = "2016",

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doi = "10.1021/acs.orglett.6b01786",

language = "English (US)",

volume = "18",

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T1 - Dual Emission and Mechanofluorochromism of a V-Shaped π-System Composed of Disulfonyl-Substituted Dibenzocyclooctatetraenes

AU - Nishida, Takanori

AU - Ohta, Shinya

AU - Xu, Feng

AU - Shinohara, Kenta

AU - Kamada, Takahiro

AU - Akashi, Haruo

AU - Takezaki, Makoto

AU - Wakamatsu, Kan

AU - Orita, Akihiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grants JP16H01164 in Middle Molecular Strategy and JP15K05440, the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. Publisher Copyright: © 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016/8/19

Y1 - 2016/8/19

N2 - A series of dibenzocyclooctatetraenes 6 bearing phenylethynyl and phenylsulfonyl groups were synthesized from bromo-substituted formylbenzyl sulfone 4 via cyclic dimerization of 4 and Sonogashira coupling of the resulting dibromocyclooctatetraene 3 with terminal acetylenes. The diamino derivative 6b exhibited dual emission with emission maxima at 436 and 547 nm. Furthermore, in the fluorescence of 6b, solvatofluorochromism was observed in response to solvent polarity, whereas in the solid states, mechanofluorochromism was observed.

AB - A series of dibenzocyclooctatetraenes 6 bearing phenylethynyl and phenylsulfonyl groups were synthesized from bromo-substituted formylbenzyl sulfone 4 via cyclic dimerization of 4 and Sonogashira coupling of the resulting dibromocyclooctatetraene 3 with terminal acetylenes. The diamino derivative 6b exhibited dual emission with emission maxima at 436 and 547 nm. Furthermore, in the fluorescence of 6b, solvatofluorochromism was observed in response to solvent polarity, whereas in the solid states, mechanofluorochromism was observed.

UR - https://www.scopus.com/pages/publications/84984683753

UR - https://www.scopus.com/pages/publications/84984683753#tab=citedBy

U2 - 10.1021/acs.orglett.6b01786

DO - 10.1021/acs.orglett.6b01786

M3 - Article

C2 - 27494278

AN - SCOPUS:84984683753

SN - 1523-7060

VL - 18

SP - 3988

EP - 3991

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Dual Emission and Mechanofluorochromism of a V-Shaped π-System Composed of Disulfonyl-Substituted Dibenzocyclooctatetraenes

Abstract

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