Synthesis, structure and anion binding properties of 1,8-bis(dimesitylboryl)anthracene and its monoborylated analog

Two boranes, 1-(dimesitylboryl)anthracene ( 1 ) and 1,8-bis(dimesitylboryl)anthracene ( 2 ), have been synthesized with the spectrophysical properties showing how the inclusion of one or two boron atoms progressively perturbs the π-system of the anthracene backbone. This perturbation is caused by co...

Full description

Saved in:
Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2019-10, Vol.48 (39), p.14777-14782
Main Authors: Teerasarunyanon, Ratanakorn, Wilkins, Lewis C, Park, Gyeongjin, Gabbaï, François P
Format: Article
Language:English
Subjects:
Anions
Anthracene
Binding
Blue shift
Boranes
Boron
Conjugation
Crystallography
Cyanides
Doppler effect
Fluorescence
Fluorides
Perturbation
Red shift
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two boranes, 1-(dimesitylboryl)anthracene ( 1 ) and 1,8-bis(dimesitylboryl)anthracene ( 2 ), have been synthesized with the spectrophysical properties showing how the inclusion of one or two boron atoms progressively perturbs the π-system of the anthracene backbone. This perturbation is caused by conjugation of the anthracene-π* orbital with the vacant p-orbital on boron. Additionally, both 1 and 2 have a high affinity for fluoride and cyanide anions which are complexed in a 1 : 1 guest-host ratio. The mono-borane 1 is particularly well-suited for cyanide binding, displaying a binding constant of 3 × 10 7 in THF. Furthermore, as a result of their unique electronic structures, these boranes display a fluorescence response to fluoride anion characterized by a blue shift in the case of 1 and a red shift in the case of 2 . 1,8-Bis(dimesitylboryl)anthracene binds the toxic fluoride and cyanide anion to afford the corresponding 1 : 1 complexes that display a red shifted emission in the green part of the spectrum.
ISSN:1477-9226
1477-9234
DOI:10.1039/c9dt03238j