Organic Letters
Letter
Jeong, J. H.; Song, J.; Lee, J. Y.; Kwon, J. H. ACS Appl. Mater. Interfaces
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function to boron presumably inhibits the third C−F bond
formation.
In summary, we designed an alkynylboration reaction leading
to an unprecedended boron-containing π-extended cis-stilbene
possessing enormous potential as a luminophore. A wide variety
of these compounds can be easily accessed by the alkynylbora-
tion of alkynamides via pseudo-intramolecular activation. The
fluorescence emission wavelength in the solid state depends on
the substituent at the acetylenic terminus, and aryl substituents
endow the enyne compound with high fluorescence quantum
yield and AIEE character. Detailed studies on the properties of
the boron-containing π-extended cis-stilbenes, focusing on
applications as molecular sensors and bioimaging, are ongoing
in our laboratory.
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
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Accession Codes
CCDC 1886119 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge via
Crystallographic Data Centre, 12 Union Road, Cambridge
CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
Corresponding Authors
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ORCID
(11) For transition-metal-free boration of propiolic acid derivatives,
see: (a) Fritzemeier, R.; Gates, A.; Guo, X.; Lin, Z.; Santos, W. L. J. Org.
Chem. 2018, 83, 10436. (b) Nagao, K.; Yamazaki, A.; Ohmiya, H.;
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Iwai, T.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2018, 57,
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(e) Verma, A.; Snead, R. F.; Dai, Y.; Slebodnick, C.; Yang, Y.; Yu, H.;
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(13) Cordero, B.; Gomez, V.; Platero-Prats, A. E.; Reves, M.;
This work was partly supported by JSPS KAKENHI (S) (No.
24229011), The Asahi Glass Foundation, Foundation NAGASE
Science Technology Development, and Sumitomo Foundation
(to M.U.), JSPS Grant-in-Aid for Young Scientists (A) (No.
16H06214) (to K.H.) and Challenging Research (Exploratory)
(No. 18K19390) (to K.H.). The calculations were performed on
the RIKEN HOKUSAI GreatWave and BigWaterfall. We thank
the Advanced Center for Computing and Communication
(RIKEN) for providing computational resources.
́
Echeverría, J.; Cremades, E.; Barragan, F.; Alvarez, S. Dalton Trans.
2008, 2832.
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