Boryl- and amino-substituted acetylenes bearing diphenylboryl or 9-borabicyclononyl groups were synthesized. X-ray diffraction analyses revealed the dimerized structures of these acetylenes via the formation of B2C2 four-membered rings. Spectroscopic studies and DFT calculations indicated that these dimers can dissociate to afford monomeric acetylenes, and that the equilibrium constant for the dissociation depends on the structure of the boryl substituents.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/c8cc02122h | DOI Listing |
Chem Sci
March 2021
Department of Chemistry, Graduate School of Science, Integrated Research Consortium on Chemical Sciences (IRCCS), Nagoya University Furo, Chikusa Nagoya 464-8602 Japan
The use of donor-π-acceptor (D-π-A) skeletons is an effective strategy for the design of fluorophores with red-shifted emission. In particular, the use of amino and boryl moieties as the electron-donating and -accepting groups, respectively, can produce dyes that exhibit high fluorescence and solvatochromism. Herein, we introduce a dithienophosphole -oxide scaffold as an acceptor-spacer to produce a boryl- and amino-substituted donor-acceptor-acceptor (D-A-A) π-system.
View Article and Find Full Text PDFChemistry
September 2020
Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &, Catalysis with Boron (ICB), Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
We synthesized a series of new mono-, di-, tri- and tetra-substituted perylene derivatives with strong bis(para-methoxyphenyl)amine (DPA) donors at the uncommon 2,5,8,11-positions. The properties of our new donor-substituted perylenes were studied in detail to establish a structure-property relationship. Interesting trends and unusual properties are observed for this series of new perylene derivatives, such as a decreasing charge transfer (CT) character with increasing number of DPA moieties and individual reversible oxidations for each DPA moiety.
View Article and Find Full Text PDFOrg Lett
June 2019
School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites , Shanghai Jiao Tong University, Shanghai 200240 , People's Republic of China.
A Brønsted-acid-promoted alkyne benzannulation approach was developed to synthesize the amino-substituted dibenze[ a, j]anthracence derivatives in excellent yields, which were directly converted to fully zigzag-edged polycyclic heteroaromatic hydrocarbons via a nitrogen-directed electrophilic borylation. As the dopant in a blue-green electroluminescent device, the resulted compound exhibited relatively high stability.
View Article and Find Full Text PDFChem Commun (Camb)
June 2018
Department of Applied Chemistry, Graduate School of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.
Boryl- and amino-substituted acetylenes bearing diphenylboryl or 9-borabicyclononyl groups were synthesized. X-ray diffraction analyses revealed the dimerized structures of these acetylenes via the formation of B2C2 four-membered rings. Spectroscopic studies and DFT calculations indicated that these dimers can dissociate to afford monomeric acetylenes, and that the equilibrium constant for the dissociation depends on the structure of the boryl substituents.
View Article and Find Full Text PDFJ Am Chem Soc
January 2010
Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
The reaction of 1,1,4,4-tetrakis[bis(trimethylsilyl)methyl]-1,4-diisopropyltetrasila-2-yne 1 with diethylamine or diphenylamine produced the corresponding amino-substituted disilenes R(R'(2)N)Si=SiHR 2a, b (R = Si(i)Pr[CH(SiMe(3))(2)](2), R' = Et (2a), Ph (2b)). The reaction of 1 with 9-borabicyclo[3.3.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!