Strong ion pair charge transfer interaction of 1,8-naphthalimide–bipyridinium conjugates with basic anions – towards the development of a new type of turn-on fluorescent anion sensors

In this work, a novel 7-hydroxybenzoxazinone-based fluorescent probe (PBD) for the selective sensing of biothiols is reported. Upon treatment with biothiols, PBD shows a strong fluorescence enhancement (up to 70-fold) and a large Stokes shift (155 nm). Meanwhile, this probe exhibits high resistance to interference from other amino acids and competing species. PBD features good linearity ranges with a low detection limit of 14.5 nM for glutathione (GSH), 17.5 nM for cysteine (Cys), and 80.0 nM for homocysteine (Hcy), respectively. Finally, the potential utility of this probe for biothiol sensing in living HeLa cells is demonstrated.

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Synthetic control over intra- and intermolecular charge transfer can turn on the fluorescence emission of non-emissive coumarin

Journal of Materials Chemistry C ◽

10.1039/c6tc00639f ◽

2016 ◽

Vol 4 (20) ◽

pp. 4556-4567 ◽

Cited By ~ 20

Author(s):

Byung Hak Jhun ◽

Kei Ohkubo ◽

Shunichi Fukuzumi ◽

Youngmin You

Keyword(s):

Charge Transfer ◽

Fluorescence Emission ◽

Synthetic Control ◽

Photoinduced Charge Transfer ◽

Strong Fluorescence ◽

Turn On ◽

Intermolecular Charge Transfer ◽

Coumarin Compounds ◽

Photoinduced Charge

Photoinduced charge transfer was exploited in coumarin compounds to obtain strong fluorescence emission.

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A Boronic Acid-Based Fluorescence Hydrogel for Monosaccharide Detection

10.26434/chemrxiv.7176989 ◽

2018 ◽

Author(s):

Suying Xu ◽

Adam Sedgwick ◽

Souad Elfecky ◽

Wenbo Chen ◽

Ashley Jones ◽

...

Keyword(s):

Fluorescent Probe ◽

Boronic Acid ◽

Binding Constants ◽

Strong Fluorescence ◽

Fluorescence Response ◽

Turn On ◽

Fluorescence Turn On ◽

Hydrogel System

A boronic acid-based anthracene fluorescent probe was functionalised with an acrylamide unit to incorporate into a hydrogel system for monosaccharide detection. In solution, the fluorescent probe displayed a strong fluorescence turn-on response upon exposure to fructose, and an expected trend in apparent binding constants, as judged by a fluorescence response where D-fructose > D-galactose > D-mannose > D-glucose. The hydrogel incorporating the boronic acid monomer demonstrated the ability to detect monosaccharides by fluorescence with the same overall trend as the monomer in solution with the addition of fructose resulting in a 10-fold enhancement (≤ 0.25 M).

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Fluorescence Quenching of Aminodiphenylamines with Chloromethanes

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20021154 ◽

2002 ◽

Vol 67 (8) ◽

pp. 1154-1164 ◽

Cited By ~ 2

Author(s):

Nachiappan Radha ◽

Meenakshisundaram Swaminathan

Keyword(s):

Charge Transfer ◽

Fluorescence Quenching ◽

Ground State ◽

Rate Constants ◽

Quenching Mechanism ◽

Quenching Rate ◽

Charge Transfer Interaction ◽

Electronically Excited ◽

A Charge

The fluorescence quenching of 2-aminodiphenylamine (2ADPA), 4-aminodiphenylamine (4ADPA) and 4,4'-diaminodiphenylamine (DADPA) with tetrachloromethane, chloroform and dichloromethane have been studied in hexane, dioxane, acetonitrile and methanol as solvents. The quenching rate constants for the process have also been obtained by measuring the lifetimes of the fluorophores. The quenching was found to be dynamic in all cases. For 2ADPA and 4ADPA, the quenching rate constants of CCl4 and CHCl3 depend on the viscosity, whereas in the case of CH2Cl2, kq depends on polarity. The quenching rate constants for DADPA with CCl4 are viscosity-dependent but the quenching with CHCl3 and CH2Cl2 depends on the polarity of the solvents. From the results, the quenching mechanism is explained by the formation of a non-emissive complex involving a charge-transfer interaction between the electronically excited fluorophores and ground-state chloromethanes.

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Anion-enhanced excited state charge separation in a spiro-locked N-heterocycle-fused push-pull zinc porphyrin

Chemical Science ◽

10.1039/d1sc00038a ◽

2021 ◽

Author(s):

Mandeep K. Chahal ◽

Anuradha Liyanage ◽

Ajyal Z. Alsaleh ◽

Paul A. Karr ◽

Jonathan P. Hill ◽

...

Keyword(s):

Excited State ◽

Charge Transfer ◽

Charge Separation ◽

Charge Transfer Complex ◽

Zinc Porphyrin ◽

New Type ◽

State Charge

A new type of push–pull charge transfer complex, viz., a spiro-locked N-heterocycle-fused zinc porphyrin, ZnP-SQ, is shown to undergo excited state charge separation, which is enhanced by axial F− binding to the Zn center.

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Enantioselective Nucleophilic Aromatic Substitution Reaction of Azlactones to Synthesize Quaternary α-Amino Acid Derivatives

Synlett ◽

10.1055/a-1323-2389 ◽

2020 ◽

Author(s):

Xiaohua Liu ◽

Yi Li ◽

Hao Pan ◽

Wang-Yuren Li ◽

Xiaoming Feng

Keyword(s):

Hydrogen Bonding ◽

Charge Transfer ◽

Amino Acid ◽

Substitution Reaction ◽

Nucleophilic Aromatic Substitution ◽

Amino Acid Derivatives ◽

Amino Acid Esters ◽

Aromatic Substitution ◽

Charge Transfer Interaction ◽

Acid Esters

AbstractAn asymmetric organocatalytic nucleophilic aromatic substitution reaction of azlactones with electron-deficient aryls was established. A variety of α-aryl α-alkyl α-amino acid esters and peptides were obtained in decent yields and stereoselectivities. A new bifunctional catalytic mode involving charge-transfer interaction and hydrogen bonding is proposed to explain the enantioselectivity.

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