New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds

Sala, Neus; Prats, G; Villabona, Marc; Gallardo, Iluminada; Hamdan, T.A.; Al‐Kaysi, Rabih O.; Hernando, Jordi; Guirado, Gonzalo

doi:10.1016/j.dyepig.2018.01.058

Cited by 7 publications

(7 citation statements)

References 27 publications

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“…An added advantage of SZMCs over other pH-responsive fluorescent switches is their capacity to undergo redox-induced interconversion between their anionic and neutral states in organic solvents such as acetonitrile or DMF. ,− Inspired by this behavior, we explored herein the reversible transformation between the neutral and cationic forms of these compounds by means of electrochemical stimuli. Because of its simpler switching scheme owing to the thermal stability of its zwitterionic state, we took compound 1 as a benchmark case for these studies.…”

Section: Resultsmentioning

confidence: 57%

“…A promising class of compounds to reach this behavior are spirocyclic zwitterionic Meisenheimer compounds (SZMC) of 1,3,5-trisubstituted benzene, a family of versatile organic fluorescent switches introduced by us several years ago. ,− The structure of these systems, inspired from the well-known Jackson–Meisenheimer intermediates of nucleophilic aromatic substitution reactions, , comprises two different functional units linked through a spiranic carbon atom: (a) a highly fluorescent, visible-light absorbing cyclohexadienyl anion group with strong electron withdrawing substituents at positions 2, 4 and 6, and (b) a triazene ring capable to respond to external stimuli (Scheme ). ,− …”

Section: Introductionmentioning

confidence: 99%

“…The use of SZMC switches offers several advantages. First, they can be prepared via a facile one-step synthetic procedure involving commercially available reactants. ,, Second, large emission modulation amplitudes are found between the fluorescent and nonfluorescent states of these systems, which in combination with the optical properties of their cyclohexadienyl anion units allow their detection with high sensitivity in the visible region of the spectrum. ,− Furthermore, they show versatile switching behavior, which can be triggered using different types of stimuli and lead to a multistate scheme. In the case of compound 1 bearing a 2,4,6-trinitrocyclohexadienyl anion, reversible interconversion between its fluorescent ( 1b ) and nonfluorescent ( 1a ) states requires protonation–deprotonation of the guanidine moiety in the triazene ring, which can be achieved either chemically upon acid–base addition or electrochemically by inducing combined electron and hydrogen transfer processes (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

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Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials

et al. 2018

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Fluorescent switches based on spirocyclic zwitterionic Meisenheimer (SZMC) complexes are stimuli-responsive organic molecules with application in a variety of areas. To expand their functionality, novel switching mechanisms are herein reported for these systems: (a) acid- and redox-triggered formation of an additional protonation state with distinct optical properties, and (b) solvent-induced fluorescence modulation. We demonstrate that these new features, which enable both multistimuli and multistate operation of SZMC switches, can be exploited in the preparation of smart organic materials: wide-range pH optical probes, electrochromic and electrofluorochromic films, and polymer-based fluorescent detectors of organic liquids.

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Section: Resultsmentioning

confidence: 57%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials

et al. 2018

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“…In contrast, thermochromic luminescent materials have attracted particular interest due to their features of easy preparation, low cost, and wide applicability. Various thermochromic luminescent materials have been successfully designed and demonstrated by many research studies, such as triarylboron molecules, spiroheterocyclic compounds, poly(ε-caprolactone) terminated with a tetraphenylethene polymer, nanocomposites with functional fluorophores, luminescent supramolecular assembly films, etc. When combined with electric heating materials, electro-thermochromic materials, including 1D fibers, could be achieved easily. − …”

Section: Introductionmentioning

confidence: 99%

Electro-Thermochromic Luminescent Fibers Controlled by Self-Crystallinity Phase Change for Advanced Smart Textiles

Duan

Wang

et al. 2021

ACS Appl. Mater. Interfaces

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Smart textiles with tunable luminescence have received special attention due to their great potential in various advanced photonic applications. Particularly, the development of one-dimensional, on-demand, responsive fluorescence fibers with excellent adaptability is of great significance. Herein, we propose electro-thermochromic fluorescence fibers regulated by a self-crystallinity phase change; that is, their tunable luminescence properties are derived from the reversible conversion of the dispersion state and fluorescence emission of fluorophore molecules during the crystallization/melting processes of phase-change materials. First results obtained with an alginate wet-spinning system demonstrate that the self-crystallinity phase change can produce polymeric fibers with thermochromic fluorescence behavior, which are prepared using microemulsion particles containing a phase-change fatty acid and coumarin fluorescent dyes. These thermochromic fluorescence fibers possess a fast response speed, high emission contrast, and good reversibility (>100 cycles). Particularly, the thermochromic fluorescent fibers can gain an electrotriggered capability by means of electric heating materials, and their great potential in precision operation applications is demonstrated. It is easy to adjust the switching point of the electro-thermochromic fluorescence fibers, highlighting their potential use in a diverse range of applications, the designs of which can be personalized. This work offers a simple yet versatile strategy for constructing electro-thermochromic fluorescence fibers for advanced smart textiles.

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“…In the category of fluorescent sensors, Meisenheimer complexes have recently attracted considerable attention. Several research groups have synthesised various stable Meisenheimer complexes of 1,3,5‐trisubstituted benzene that are capable of responding to more than one stimulus 34‐38 . The structure of these compounds is based on the Jackson–Meisenheimer intermediates of aromatic nucleophilic substitution reactions 39,40 .…”

Section: Introductionmentioning

confidence: 99%

Colorimetric sensing of acidic vapour through protonation of a Meisenheimer complex

Das

Mohar

2020

Coloration Technology

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In the current work, we investigate the mechanism of protonation of a Meisenheimer complex derived from picric acid and N,N′‐dicyclohexylcarbodiimide to provide the correct structure of the protonated Meisenheimer complex with the proper mechanism. A substituted picramide derivative has also been synthesised and characterised using various spectroscopic techniques to rule out the previously suggested protonated Meisenheimer complexes and support our proposed protonated structure. Various other investigations, including the interactions of the Meisenheimer complex with bulky electrophile Lawesson's reagent and bulky Lewis acid Eu(fod)3, were also carried out to support the mechanism of protonation. Various bulky bases as well as bases of different strengths were treated with the protonated Meisenheimer complex to support our proposed structure. Based on the protonation of the Meisenheimer complex, a general colorimetric volatile acid sensor has been designed, where a distinct colour change from orange to colourless was found to take place after protonation. The sensor can detect volatile acids both in the solid and in the solution state. The sensor was also applied to detect hydrogen chloride vapour in an automated manner using a smartphone, where information regarding the leakage position can be obtained through wireless communication. The detection limit of hydrogen chloride vapour was found to be 43.5 ppm.

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New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds

Cited by 7 publications

References 27 publications

Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials

Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials

Electro-Thermochromic Luminescent Fibers Controlled by Self-Crystallinity Phase Change for Advanced Smart Textiles

Colorimetric sensing of acidic vapour through protonation of a Meisenheimer complex

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