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797367

Sigma-Aldrich

[(1,2-Diphenylethene-1,2-diyl)bis(4,1-phenylene)]diboronic acid

Synonym(s):

TPE-BA

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About This Item

Empirical Formula (Hill Notation):
C26H22B2O4
CAS Number:
1054451-31-8
Molecular Weight:
420.07
UNSPSC Code:
12352103
PubChem Substance ID:
329768590
NACRES:
NA.23

assay

96%

form

solid

storage temp.

2-8°C

SMILES string

OB(O)C(C=C1)=CC=C1/C(C2=CC=CC=C2)=C(C3=CC=C(B(O)O)C=C3)\C4=CC=CC=C4

InChI

1S/C26H22B2O4/c29-27(30)23-15-11-21(12-16-23)25(19-7-3-1-4-8-19)26(20-9-5-2-6-10-20)22-13-17-24(18-14-22)28(31)32/h1-18,29-32H/b26-25+

InChI key

CFKHFTZRFSABDV-OCEACIFDSA-N

General description

Aggregation-induced emission luminogens (AIEgens) such as tetraphenylethene (TPE) functionalized with boronic acids form luminogen (TPE-BA). TPE-BA can form oligoboronates with D-glucose. Other sugars also form monoadduct with TPE-BA, but once such a complex is formed there is no more cis-diol that allows the oligomerization reaction to proceed, resulting in a very low emission intensity. Thus, TPE-BA could serve as a glucose-specific probe.

Application

TPE-BA is an aggregation-induced emission (AIE) dye for use in Suzuki reaction and D-Glucose detection.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD3632

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Yi Liu et al.
Journal of the American Chemical Society, 133(4), 660-663 (2010-12-22)
A conceptually new "light-up" biosensor with a high specificity for d-glucose (Glu) in aqueous media has been developed. The emission from a tetraphenylethene (TPE)-cored diboronic acid (1) was greatly boosted when the fluorogen was oligomerized with Glu because of restriction

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