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Title: Distiboranes based on ortho -phenylene backbones as bidentate Lewis acids for fluoride anion chelation
As part of our efforts in the chemistry of main group platforms that support anion sensing and transport, we are now reporting the synthesis of anitmony-based bidentate Lewis acids featuring the o -C 6 F 4 backbone. These compounds can be easily accessed by reaction of the newly synthesized o -C 6 F 4 (SbPh 2 ) 2 ( 5 ) with o -chloranil or octafluorophenanthra-9,10-quinone, affording the corresponding distiboranes 6 and 7 of general formula o -C 6 F 4 (SbPh 2 (diolate)) 2 with diolate = tetrachlorocatecholate for 6 and octafluorophenanthrene-9,10-diolate for 7 , respectively. While 6 is very poorly soluble, its octafluorophenanthrene-9,10-diolate analog 7 readily dissolves in CH 2 Cl 2 and undergoes swift conversion into the corresponding fluoride chelate complex [ 7 -μ 2 -F] − which has been isolated as a [ n Bu 4 N] + salt. The o -C 6 H 4 analog of 7 , referred to as 8 , has also been prepared. Although less Lewis acidic than 7 , 8 also forms a very stable fluoride chelate complex ([ 8 -μ 2 -F] − ). Altogether, our experiental results, coupled with computational analyses and fluoride anion affinity calculations, show that 7 and 8 are some of the strongest antimony-based fluoride anion chelators prepared to date. Another notable aspect of this work concerns the use of the octafluorophenanthrene-9,10-diolate ligand and its ablity to impart advantageous solubility and Lewis acidity properties.  more » « less
Award ID(s):
1856453
PAR ID:
10248512
Author(s) / Creator(s):
; ; ;
Date Published:
Journal Name:
Organic & Biomolecular Chemistry
Volume:
19
Issue:
22
ISSN:
1477-0520
Page Range / eLocation ID:
4949 to 4957
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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