Fluoride Ion-Triggered Dual Fluorescence Switch Based on Naphthalimides Winged Zinc Porphyrin

Li, Yang; Cao, Lifeng; Tian, He

doi:10.1021/jo061161+

Cited by 116 publications

(44 citation statements)

References 45 publications

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“…Further utilising this deprotonation mechanism, Tian et al 64 have also covalently attached two 4-amido-1,8-naphthalimide fluorophores to a zinc porphyrin core resulting in a novel F À ion triggered dual fluorescent molecular switch, 22. The absorption spectrum of 22 consisted of a naphthalimide absorption at ca.…”

Section: Urea and Thiourea-based 4-amido-18-naphthalimide-based Aniomentioning

confidence: 99%

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

et al. 2010

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This critical review focuses on the development of anion sensors, being either fluorescent and/or colorimetric, based on the use of the 1,8-naphthalimide structure; a highly versatile building unit that absorbs and emits at long wavelengths. The review commences with a short description of the most commonly used design principles employed in chemosensors, followed by a discussion on the photophysical properties of the 4-amino-1,8-naphthalimide structure which has been most commonly employed in both cation and anion sensing to date. This is followed by a review of the current state of the art in naphthalimide-based anion sensing, where systems using ureas, thioureas and amides as hydrogen-bonding receptors, as well as charged receptors have been used for anion sensing in both organic and aqueous solutions, or within various polymeric networks, such as hydrogels. The review concludes with some current and future perspectives including the use of the naphthalimides for sensing small biomolecules, such as amino acids, as well as probes for incorporation and binding to proteins; and for the recognition/sensing of polyanions such as DNA, and their potential use as novel therapeutic and diagnostic agents (95 references).

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Section: Urea and Thiourea-based 4-amido-18-naphthalimide-based Aniomentioning

confidence: 99%

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

et al. 2010

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“…[9][10][11][12][13][14][15][16] Their excited states are characterized by a "push-pull" internal charge transfer (ICT) character, arising from the presence of the electron-withdrawing imide and the electron donating amino moiety; this being strongest where the amino group is in the 4-position of the ring. 9,[15][16][17][18][19] Because of this they have also been employed as potential cellular imaging and antitumor agents. 20 In this context, we have also reported development of DNA photocleavage agents based on 4-amino-1,8-naphthalimide conjugated with ruthenium(II) complex, 19 and we have prepared Tröger's base derivatives of the 4-amino-1,8-naphthalimide structure and shown these to be efficient DNA binders, and cytotoxic agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

et al. 2012

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The synthesis, characterisation and solid state crystal structure of a cationic 4-amino-1,8-naphthalimide derivative (1) are described. The photophysical properties of 1 are shown to vary with the solvent polarity and H-bonding ability. The fluorescence of 1 is enhanced and blue-shifted in its 1 : 1 complex with 5′-adenosine-monophosphate while it is partially quenched and red-shifted in its complex with 5′-guanosine-monophosphate. Linear and circular dichroism measurements show that 1 binds to double-stranded DNA by intercalation. Comparative UV-visible and fluorescence studies with double stranded synthetic polynucleotides poly(dA-dT) 2 and poly(dG-dC) 2 show that 1 binds much more strongly to the AT polymer; 1 also has a strong preference for A-T rich sequences in natural DNA. Thermal denaturation measurements also reveal a much greater stabilisation of the double-stranded poly (dA-dT) 2 than of natural DNA.

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“…And some of them have been used as fluorescent chemosensors for metal cations, [14][15][16][17] anions 18,19 and pH [20][21][22][23] in recent years. These make naphthalimide derivatives potential carriers for preparation of new optical chemosensors.…”

Section: Introductionmentioning

confidence: 99%

A Fluorescent pH Chemosensor Based on Functionalized Naphthalimide in Aqueous Solution

Zhou

et al. 2012

ANAL. SCI.

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Fluoride Ion-Triggered Dual Fluorescence Switch Based on Naphthalimides Winged Zinc Porphyrin

Cited by 116 publications

References 45 publications

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

A Fluorescent pH Chemosensor Based on Functionalized Naphthalimide in Aqueous Solution

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