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Non Boronic acid glucose

sensors

(c)carboxyl-modified
(a)calixarene (b)phosphonate graphene oxide (GO-
framework,perfect for face- moieties as COOH) has peroxidase-
to-face recognition receptors for like activity and can
between the calixarenes
upper-rim hydroxyls and
saccharides, such catalyze reaction of the
those of the saccharide asthe rigid chiral peroxidase substrate
spirobifluorene 3,3,5,5-
a) Aoyama, Y.; Tanaka, Y.; Toi, H.; Ogoshi, H.J. Am. Chem. Soc. 1988, tetramethylbenzidine
110, 634 (TMB) to produce a blue
b) Das, G.; Hamilton, A. D. Tetrahedron Lett. 1997, 38, 3675 color in the presence of
Boronic acid based sensors
a) Cyclic boric and boronic esters are c) Saccharide recognition via boronic acid
formed when boronic acids react with complex (or boronic ester) formation frequently
saccharides
relies on the interaction between aboronic acid
(Lewis acidic) and a neighboring tertiary amine
(Lewis basic).
d) Saccharide binding strengthens the NB
interaction (caused by an increase in Lewis
acidity of the boron upon saccharide binding),
b) Lewis acidic nature of boron has resulting in modulation of the fluorescence of
resulted in the development of receptors nearby fluorophores (since the fluorescent
and sensors for anions photoinduced electron transfer (PET) from the
nitrogen is controlled by the strength of the NB
interaction).

a) Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769


b) (1) Nishiyabu, R.; Kubo, Y.; James, T. D.; Fossey, J. S. Chem. Commun. 2011, 47, 1106.
(2)Hudnall, T. W.; Chiu, C.-W.; Gabbai, F. P. Acc. Chem. Res. 2009, 42, 388.
c,d) Larkin, J. D.; Fossey, J. S.; James, T. D.; Brooks, B. R.; Bock, C. W.J. Phys. Chem. A 2010, 114,
Fluorescence for Sensing Applications
a)The excited state internal charge transfer (ICT) sensor consists of
a boronic acid unit directly linked to the fluorescent unit.

Anthracene derivative Stilbene boronic acid derivative

b) The naphthalimide
fluorophore has long
excitation and
emission wavelengths.

a) Yoon, J.; Czarnik, A. W. J. Am. Chem. Soc. 1992, 114, 5874.


b) Cao, H.; Diaz, D. I.; DiCesare, N.; Lakowicz, J. R.; Heagy, M. D. Org. Lett.
2002, 4, 1503.
c) ) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S.Angew. Chem., Int. Ed.