Fluorescence Fluoride Ion Sensor Utilizing Desilylation of N-Silylated 9- Aminoanthracene

N,N-Bis(trimethylsilyl)-9-aminoanthracene (Si9AA) was synthesized by deprotonation of 9-aminoanthracne (9AA) with n-BuLi followed by the addition of trimethylsilyl chloride (TMSCl). Under ultraviolet, Si9AA showed blue fluorescence originated from the anthracene skeleton due to orthogonal relation between anthracene skeleton and bis(trimethylsilyl)amino group, which was determined by X-ray crystallographic analysis, while 9AA, in which conjugation exists between the anthracene and the amino group, showed green fluorescence. In a THF solution, Si9AA was converted to 9AA by desilylation of bis(trimethylsilyl)amino group with fluoride ion, which was contained in tetrabutylammonium fluoride (TBAF) or KF-18-crown-6 complex, resulting in fluorescence color change from blue to green. Si9AA was found to utilize as a sensor to detect fluoride ion in THF solution or on a thin layer chromatography (TLC) via the fluorescence color change without any metals, regarding a metal free fluorescence fluoride sensor in green chemistry.

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ChemInform Abstract: “ANHYDROUS” TETRABUTYLAMMONIUM FLUORIDE: A MILD BUT HIGHLY EFFICIENT SOURCE OF NUCLEOPHILIC FLUORIDE ION

Chemischer Informationsdienst ◽

10.1002/chin.198506122 ◽

1985 ◽

Vol 16 (6) ◽

Author(s):

D. P. COX ◽

J. TERPINSKI ◽

W. LAWRYNOWICZ

Keyword(s):

Fluoride Ion ◽

Highly Efficient ◽

Tetrabutylammonium Fluoride

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Fluorescence Color Change of a Boron-Substituted Diarylazomethine by Reaction with a Cyanide Ion

Bulletin of the Chemical Society of Japan ◽

10.1246/bcsj.20100145 ◽

2010 ◽

Vol 83 (10) ◽

pp. 1185-1187 ◽

Cited By ~ 8

Author(s):

Junro Yoshino ◽

Naokazu Kano ◽

Takayuki Kawashima

Keyword(s):

Color Change ◽

Cyanide Ion ◽

Fluorescence Color

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Fluorescence Color Change of Aggregation-Induced Emission of 4-[Bis(4-methylphenyl)amino]benzaldehyde

ChemPhysChem ◽

10.1002/cphc.201300781 ◽

2013 ◽

Vol 14 (17) ◽

pp. 3898-3901 ◽

Cited By ~ 19

Author(s):

Motoki Kurita ◽

Mika Momma ◽

Kei Mizuguchi ◽

Hideyuki Nakano

Keyword(s):

Color Change ◽

Aggregation Induced Emission ◽

Fluorescence Color

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Ultra‐pH‐Sensitive Small Molecule Probe Showing a Ratiometric Fluorescence Color Change

ChemPhotoChem ◽

10.1002/cptc.202000023 ◽

2020 ◽

Vol 4 (6) ◽

pp. 393-397 ◽

Cited By ~ 2

Author(s):

Junjie Cui ◽

Gayoung Kim ◽

Sehoon Kim ◽

Ji Eon Kwon ◽

Soo Young Park

Keyword(s):

Small Molecule ◽

Color Change ◽

Ph Sensitive ◽

Ratiometric Fluorescence ◽

Fluorescence Color ◽

Small Molecule Probe

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A naked-eye, selective and sensitive chemosensor for fluoride ion

Chemical Papers ◽

10.2478/s11696-010-0060-4 ◽

2010 ◽

Vol 64 (6) ◽

Cited By ~ 5

Author(s):

Puhui Xie ◽

Fengqi Guo ◽

Weifeng Wang ◽

Xiyang Liu

Keyword(s):

Charge Transfer ◽

Fluorescence Quenching ◽

Fluorescence Spectra ◽

Color Change ◽

Fluoride Ion ◽

Absorption And Fluorescence Spectra ◽

Strong Fluorescence ◽

Naked Eye ◽

Acridine Yellow ◽

Intermolecular Charge Transfer

AbstractEffect of the addition of six different anions on the absorption and fluorescence spectra of acridine yellow G (AYG) was examined. Only the F− anion could induce a visible color change observable with naked eye and a strong fluorescence quenching with K SV of 8.3 × 104 mol−1 L in CH3CN solutions. Calculated results of the interaction between the F− anion and acridine yellow G using the B3LYP/6-31G(d) program showed that the intermolecular charge transfer through the formation of an H-bond between AYG and F− is an essential sensor mechanism.

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Protonation-induced color change of an amino group functionalized [Fe 4 (μ 3 -O) 2 ] 8+ cluster

Dyes and Pigments ◽

10.1016/j.dyepig.2017.04.051 ◽

2017 ◽

Vol 143 ◽

pp. 239-244 ◽

Cited By ~ 17

Author(s):

Yang-Hui Luo ◽

Chen Chen ◽

Yao-Jia Li ◽

Jing-Wen Wang ◽

Bai-Wang Sun

Keyword(s):

Color Change ◽

Amino Group

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"Anhydrous" tetrabutylammonium fluoride: a mild but highly efficient source of nucleophilic fluoride ion

The Journal of Organic Chemistry ◽

10.1021/jo00191a035 ◽

1984 ◽

Vol 49 (17) ◽

pp. 3216-3219 ◽

Cited By ~ 196

Author(s):

D. Phillip Cox ◽

Jacek Terpinski ◽

Witold Lawrynowicz

Keyword(s):

Fluoride Ion ◽

Highly Efficient ◽

Tetrabutylammonium Fluoride

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A confined carbon dot-based self-calibrated fluorescence probe for visible and high-sensitivity moisture readouts

Journal of Physics D Applied Physics ◽

10.1088/1361-6463/ac3e8f ◽

2021 ◽

Author(s):

Zhong-Zheng Ding ◽

Guang-Song Zheng ◽

Qing Lou ◽

Jiang-Fan Han ◽

Meng-Yuan Wu ◽

...

Keyword(s):

High Performance ◽

Potential Role ◽

Fluorescence Probe ◽

Color Change ◽

High Sensitivity ◽

Confinement Effect ◽

Detection Range ◽

Fluorescence Color ◽

Highly Sensitive ◽

New Type

Abstract Excellent luminescent materials are essential for high-performance fluorescent nanosensors. Here, a new-type self-calibrated humidity sensor has been established through monitoring the fluorescent color change of carbon dots (CDs) confined in sodium hydroxide (CDs@NaOH). The CDs are prepared by a facile and rapid microwave assisted heating method using citric acid, urea, and NaOH as precursors. The confinement effect from NaOH has reduced the nonradiative transition and suppressed the aggregation-induced quenching of the CDs in solid. Compared with other sensors based on CD fluorescent visualization, the sensor has good linearity and wide humidity detection range from 6.9% to 95.4%. With the increased relative humidity, the fluorescence color of the sensor change from green to blue. The proposed sensing mechanism is due to the breaking and reforming of hydrogen bonds and proton transfer occurring at the CD-NaOH matrix interfaces. This finding suggests a potential role for the spatial confinement effect and may provide an avenue for developing highly sensitive humidity readouts.

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Detection of the Potential Adulterant Teucrium chamaedrys in Scutellaria baicalensis Raw Material and Extract by High-Performance Thin-Layer Chromatography

Journal of AOAC International ◽

10.1093/jaoac/92.3.785 ◽

2009 ◽

Vol 92 (3) ◽

pp. 785-788 ◽

Cited By ~ 3

Author(s):

Thao Hong ◽

Mijeong Lee Jeong ◽

Michael Zahn ◽

Brooke A Fay ◽

Kangwoo Lee ◽

...

Keyword(s):

Thin Layer ◽

High Performance ◽

Raw Material ◽

Green Fluorescence ◽

Simple Method ◽

Bright Green ◽

Teucrium Chamaedrys ◽

Layer Chromatography ◽

Bright Green Fluorescence ◽

Hptlc Method

Abstract Teucrium chamaedrys (Gemander) has been reported as an adulterant of Scutellaria lateriflora (American skullcap) herbal preparations and is also known to be hepatotoxic. A quick and simple high-performance thin-layer chromatographic (HPTLC) method was developed for the detection of T. chamaedrys (Germander) in S. baicalensis (Chinese skullcap) extract, an ingredient of the proprietary blend product, Univestin. The HPTLC profile of T. chamaedrys was distinguished from that of S. baicalensis by its bright green fluorescence bands. This simple method can be completed in an hour for the quality control of Univestin and its raw material, S. baicalensis. The method is sensitive and can detect T. chamaedrys at levels as low as 0.5 (w/w).

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