Deoxyribonucleoside-modified squaraines as near-IR viscosity sensors

Yuanwei Zhang; Xiling Yue; Bosung Kim; Sheng Yao; Kevin D. Belfield

doi:10.1002/chem.201403003

Deoxyribonucleoside-modified squaraines as near-IR viscosity sensors

Yuanwei Zhang, Xiling Yue, Bosung Kim, Sheng Yao, Kevin D. Belfield

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

20 Scopus citations

Abstract

Deoxyribonucleoside-modified squaraines were synthesized by Sonogashira coupling reactions using an unsymmetrical, terminal alkynylated benzothiazolium squaraine dye. These non-natural nucleosides exhibited fluorescent 'turn-on' properties in viscous conditions with an enhancement of >300-fold. The viscosity-dependent fluorescence enhancement was attributed to a combination of hampering both molecular aggregation and intramolecular bond rotation of the squaraine probe. Fluorescence microscopy allowed visualization of highly viscous regions during various stages of cellular mitosis.

Original language	English (US)
Pages (from-to)	7249-7253
Number of pages	5
Journal	Chemistry - A European Journal
Volume	20
Issue number	24
DOIs	https://doi.org/10.1002/chem.201403003
State	Published - Jun 10 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Keywords

aggregation
deoxyribonucleosides
near-IR imaging
squaraine dyes
viscosity sensors

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10.1002/chem.201403003

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title = "Deoxyribonucleoside-modified squaraines as near-IR viscosity sensors",

abstract = "Deoxyribonucleoside-modified squaraines were synthesized by Sonogashira coupling reactions using an unsymmetrical, terminal alkynylated benzothiazolium squaraine dye. These non-natural nucleosides exhibited fluorescent 'turn-on' properties in viscous conditions with an enhancement of >300-fold. The viscosity-dependent fluorescence enhancement was attributed to a combination of hampering both molecular aggregation and intramolecular bond rotation of the squaraine probe. Fluorescence microscopy allowed visualization of highly viscous regions during various stages of cellular mitosis.",

keywords = "aggregation, deoxyribonucleosides, near-IR imaging, squaraine dyes, viscosity sensors",

author = "Yuanwei Zhang and Xiling Yue and Bosung Kim and Sheng Yao and Belfield, \{Kevin D.\}",

year = "2014",

month = jun,

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doi = "10.1002/chem.201403003",

language = "English (US)",

volume = "20",

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journal = "Chemistry - A European Journal",

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T1 - Deoxyribonucleoside-modified squaraines as near-IR viscosity sensors

AU - Zhang, Yuanwei

AU - Yue, Xiling

AU - Kim, Bosung

AU - Yao, Sheng

AU - Belfield, Kevin D.

PY - 2014/6/10

Y1 - 2014/6/10

N2 - Deoxyribonucleoside-modified squaraines were synthesized by Sonogashira coupling reactions using an unsymmetrical, terminal alkynylated benzothiazolium squaraine dye. These non-natural nucleosides exhibited fluorescent 'turn-on' properties in viscous conditions with an enhancement of >300-fold. The viscosity-dependent fluorescence enhancement was attributed to a combination of hampering both molecular aggregation and intramolecular bond rotation of the squaraine probe. Fluorescence microscopy allowed visualization of highly viscous regions during various stages of cellular mitosis.

AB - Deoxyribonucleoside-modified squaraines were synthesized by Sonogashira coupling reactions using an unsymmetrical, terminal alkynylated benzothiazolium squaraine dye. These non-natural nucleosides exhibited fluorescent 'turn-on' properties in viscous conditions with an enhancement of >300-fold. The viscosity-dependent fluorescence enhancement was attributed to a combination of hampering both molecular aggregation and intramolecular bond rotation of the squaraine probe. Fluorescence microscopy allowed visualization of highly viscous regions during various stages of cellular mitosis.

KW - aggregation

KW - deoxyribonucleosides

KW - near-IR imaging

KW - squaraine dyes

KW - viscosity sensors

UR - https://www.scopus.com/pages/publications/84902141873

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U2 - 10.1002/chem.201403003

DO - 10.1002/chem.201403003

M3 - Article

C2 - 24889186

AN - SCOPUS:84902141873

SN - 0947-6539

VL - 20

SP - 7249

EP - 7253

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 24

ER -

Deoxyribonucleoside-modified squaraines as near-IR viscosity sensors

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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