Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N-Phenyl-1,8-naphthalenedicarboximides

Haishi Cao; Tom McGill; Michael D. Heagy

doi:10.1021/jo035760h

Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N-Phenyl-1,8-naphthalenedicarboximides

Haishi Cao, Tom McGill, Michael D. Heagy

Research output: Contribution to journal › Article › peer-review

65 Scopus citations

Abstract

In the course of our investigations on new monoboronic acid saccharide sensors with C₀ spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. Sensor 1 displays features typical of PET monoboronic acid sensors and shows high selectivity to fructose. Sensor 2 exhibits a novel dual emission and remarkable sensitivity for glucose relative to fructose and galactose through subtle changes in pH. Sensor 3 displays significantly enhanced fluorescence in the presence of galactose at low pH. Although probes 4-6 exhibit unique properties such as high quantum yield (φ_F = 0.407) and excellent solubility in water, they did not show significant change in fluorescence intensity in the presence of monosaccharides. The effects of substituent on all six probes lend support to the proposed photoelectrochemical model.

Original language	English (US)
Pages (from-to)	2959-2966
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	69
Issue number	9
DOIs	https://doi.org/10.1021/jo035760h
State	Published - Apr 30 2004
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo035760h

Cite this

@article{4e1d152fbd5041398e9c7744288b9d74,

title = "Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N-Phenyl-1,8-naphthalenedicarboximides",

abstract = "In the course of our investigations on new monoboronic acid saccharide sensors with C0 spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. Sensor 1 displays features typical of PET monoboronic acid sensors and shows high selectivity to fructose. Sensor 2 exhibits a novel dual emission and remarkable sensitivity for glucose relative to fructose and galactose through subtle changes in pH. Sensor 3 displays significantly enhanced fluorescence in the presence of galactose at low pH. Although probes 4-6 exhibit unique properties such as high quantum yield (φF = 0.407) and excellent solubility in water, they did not show significant change in fluorescence intensity in the presence of monosaccharides. The effects of substituent on all six probes lend support to the proposed photoelectrochemical model.",

author = "Haishi Cao and Tom McGill and Heagy, {Michael D.}",

year = "2004",

month = apr,

day = "30",

doi = "10.1021/jo035760h",

language = "English (US)",

volume = "69",

pages = "2959--2966",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N-Phenyl-1,8-naphthalenedicarboximides

AU - Cao, Haishi

AU - McGill, Tom

AU - Heagy, Michael D.

PY - 2004/4/30

Y1 - 2004/4/30

N2 - In the course of our investigations on new monoboronic acid saccharide sensors with C0 spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. Sensor 1 displays features typical of PET monoboronic acid sensors and shows high selectivity to fructose. Sensor 2 exhibits a novel dual emission and remarkable sensitivity for glucose relative to fructose and galactose through subtle changes in pH. Sensor 3 displays significantly enhanced fluorescence in the presence of galactose at low pH. Although probes 4-6 exhibit unique properties such as high quantum yield (φF = 0.407) and excellent solubility in water, they did not show significant change in fluorescence intensity in the presence of monosaccharides. The effects of substituent on all six probes lend support to the proposed photoelectrochemical model.

AB - In the course of our investigations on new monoboronic acid saccharide sensors with C0 spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. Sensor 1 displays features typical of PET monoboronic acid sensors and shows high selectivity to fructose. Sensor 2 exhibits a novel dual emission and remarkable sensitivity for glucose relative to fructose and galactose through subtle changes in pH. Sensor 3 displays significantly enhanced fluorescence in the presence of galactose at low pH. Although probes 4-6 exhibit unique properties such as high quantum yield (φF = 0.407) and excellent solubility in water, they did not show significant change in fluorescence intensity in the presence of monosaccharides. The effects of substituent on all six probes lend support to the proposed photoelectrochemical model.

UR - http://www.scopus.com/inward/record.url?scp=2142751609&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=2142751609&partnerID=8YFLogxK

U2 - 10.1021/jo035760h

DO - 10.1021/jo035760h

M3 - Article

C2 - 15104432

AN - SCOPUS:2142751609

SN - 0022-3263

VL - 69

SP - 2959

EP - 2966

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N-Phenyl-1,8-naphthalenedicarboximides

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this