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Stimuli-Responsive Chromophores and Luminophores
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Stimuli-Responsive Chromophores and Luminophores

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Colorants".

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 23520

Special Issue Editor

Prof. Dr. Barbara Panunzi

E-Mail Website
Guest Editor
Department of Agriculture, University of Napoli Federico II, 80138 Napoli, Italy
Interests: dye-sensitized solar cells (DSSC); organic semiconductors; organic fluorescent molecules; metallo-organic fluorescent materials; crystal engineering; crystal structures; optical materials; second-order NLO molecules; dyes and pigments; flurophore/chromophore probes; chemosensor; solid-state emitters; fluorescent dyes
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

As colorant we mean a substance able to produce a visible and naked eye appreciable color by absorbing an amount of light in the electromagnetic spectrum and transmitting the remaining light. Traditional employ of dyes and chromophores are printing, painting, and coloring of several substrates. The modern employ of molecules able to produce a color goes far beyond simple use as pigments, ranging from uses for electro-optical devices to optical sensors. Both chromophores and luminophores (as molecules able to provide a colorimetric response in absorbance or in emission, respectively) can be involved in the production of stimuli-responsive materials.   
This Special Issue intends to provide a forum reporting the state-of-the-art about stimuli-responsive chromophores and luminophores.  Organic, inorganic, and hybrid systems will be considered with a broad approach in the fields of chemistry, chemical engineering, and materials science. Experimental studies on design and synthesis, analytical chemistry applications, sensing properties and/or analytical separation are welcome. Systematic studies on physicochemical and thermophysical properties, as well as thermodynamics analysis will be considered. Molecular simulation studies, including DFT analysis and molecular dynamics, and finally X-Ray crystals analysis will be considered. Articles reporting novel applications for chemical, biological, environmental, and medicinal applications are especially welcome.  Review articles cut in an original way will be considered.
We hope that this Special Issue will focus the potential and the novelty of color-vectors molecules in the optical transduction techniques and will provide new directions in the technological applications.

Prof. Dr. Barbara Panunzi
Guest Editor

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Dyes
  • Chromophores
  • Luminophores
  • Fluorophores
  • Sensing
  • Synthetic route
  • Complex
  • Technological Applications

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Related Special Issue

Published Papers (8 papers)

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Research

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15 pages, 1359 KiB  
Article
Insights into Two Novel Orthopalladated Chromophores with Antimicrobial Activity against Escherichia coli
by Rosita Diana, Francesco Silvio Gentile, Antonio Carella, Luigi Di Costanzo and Barbara Panunzi
Molecules 2022, 27(18), 6060; https://doi.org/10.3390/molecules27186060 - 16 Sep 2022
Cited by 4 | Viewed by 1961
Abstract
Advanced chromophoric tools, besides being biologically active, need to meet the expectations of the technological demands including stability, colour retention, and proper solubility for their target. Many coordination compounds of conjugated ligands are antibacterial dyes, able to combine a strong dyeing performance with [...] Read more.
Advanced chromophoric tools, besides being biologically active, need to meet the expectations of the technological demands including stability, colour retention, and proper solubility for their target. Many coordination compounds of conjugated ligands are antibacterial dyes, able to combine a strong dyeing performance with a useful biological activity. Specifically, palladium (II) complexes of Schiff base ligands are known for their relevant activity against common bacteria. In this article, we report the synthesis and comprehensive experimental and theoretical characterization of two novel Pd(II) chromophore complexes obtained from a cyclopalladated Schiff base as two different chelating azo dyes. The antibacterial response of these two novel complexes was tested against the ubiquitous Escherichia coli bacterium in an aqueous medium and revealed a noteworthy antimicrobial activity, higher than when compared with their uncoordinated biologically active ligands. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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11 pages, 2347 KiB  
Article
A Highly Water-Soluble and Solid State Emissive 1,8-Naphthalimide as a Fluorescent PET Probe for Determination of pHs, Acid/Base Vapors, and Water Content in Organic Solvents
by Nikolai I. Georgiev, Paoleta V. Krasteva, Ventsislav V. Bakov and Vladimir B. Bojinov
Molecules 2022, 27(13), 4229; https://doi.org/10.3390/molecules27134229 - 30 Jun 2022
Cited by 10 | Viewed by 2492
Abstract
A new highly water-soluble 1,8-naphthalimide fluorophore designed on the “fluorophore-spacer-receptor1-receptor2” model has been synthesized. Due to the unusually high solubility in water, the novel compound proved to be a selective PET-based probe for the determination of pHs in [...] Read more.
A new highly water-soluble 1,8-naphthalimide fluorophore designed on the “fluorophore-spacer-receptor1-receptor2” model has been synthesized. Due to the unusually high solubility in water, the novel compound proved to be a selective PET-based probe for the determination of pHs in aqueous solutions and rapid detection of water content in organic solvents. Based on the pH dependence of the probe and its high water solubility, the INH logic gate was achieved using NaOH and water as chemical inputs, where NaOH is the disabler and the water is an enabler. In addition, the probe showed effective fluorescence “off-on” reversibility on glass support after exposure to acid and base vapors, which defines it as a promising platform for rapid detection of acid/base vapors in the solid-state, thus extending the molecular sensing concept from solution to the solid support. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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11 pages, 1538 KiB  
Article
Equilibrium Studies of Iron (III) Complexes with Either Pyrazine, Quinoxaline, or Phenazine and Their Catecholase Activity in Methanol
by José J. N. Segoviano-Garfias, Gabriela A. Zanor, Fidel Ávila-Ramos and Egla Yareth Bivián-Castro
Molecules 2022, 27(10), 3257; https://doi.org/10.3390/molecules27103257 - 19 May 2022
Cited by 3 | Viewed by 1941
Abstract
Currently, catalysts with oxidative activity are required to create valuable chemical, agrochemical, and pharmaceutical products. The catechol oxidase activity is a model reaction that can reveal new oxidative catalysts. The use of complexes as catalysts using iron (III) and structurally simple ligands such [...] Read more.
Currently, catalysts with oxidative activity are required to create valuable chemical, agrochemical, and pharmaceutical products. The catechol oxidase activity is a model reaction that can reveal new oxidative catalysts. The use of complexes as catalysts using iron (III) and structurally simple ligands such as pyrazine (pz), quinoxaline (qx), and phenazine (fz) has not been fully explored. To characterize the composition of the solution and identify the abundant species which were used to catalyze the catechol oxidation, the distribution diagrams of these species were obtained by an equilibrium study using a modified Job method in the HypSpec software. This allows to obtain also the UV-vis spectra calculated and the formation constants for the mononuclear and binuclear complexes with Fe3+ including: [Fe(pz)]3+, [Fe2(pz)]6+, [Fe(qx)]3+, [Fe2(qx)]6+, [Fe(fz)]3+, and [Fe2(fz)]6+. The formation constants obtained were log β110 = 3.2 ± 0.1, log β210 = 6.9 ± 0.1, log β110 = 4.4 ± 0.1, log β210 = 8.3 ± 0.1, log β110 = 6.4 ± 0.2, and log β210 = 9.9 ± 0.2, respectively. The determination of the catechol oxidase activity for these complexes did not follow a traditional Michaelis–Menten behavior. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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19 pages, 4406 KiB  
Article
Thermo-Induced Fluorochromism in Two AIE Zinc Complexes: A Deep Insight into the Structure-Property Relationship
by Rosita Diana, Ugo Caruso, Francesco Silvio Gentile, Luigi Di Costanzo, Pellegrino Musto and Barbara Panunzi
Molecules 2022, 27(8), 2551; https://doi.org/10.3390/molecules27082551 - 14 Apr 2022
Cited by 4 | Viewed by 2503
Abstract
Solid-state emitters exhibiting mechano-fluorochromic or thermo-fluorochromic responses represent the foundation of smart tools for novel technological applications. Among fluorochromic (FC) materials, solid-state emissive coordination complexes offer a variety of fluorescence responses related to the dynamic of noncovalent metal-ligand coordination bonds. Relevant FC behaviour [...] Read more.
Solid-state emitters exhibiting mechano-fluorochromic or thermo-fluorochromic responses represent the foundation of smart tools for novel technological applications. Among fluorochromic (FC) materials, solid-state emissive coordination complexes offer a variety of fluorescence responses related to the dynamic of noncovalent metal-ligand coordination bonds. Relevant FC behaviour can result from the targeted choice of metal cation and ligands. Herein, we report the synthesis and characterization of two different colour emitters consisting of zinc complexes obtained from N,O bidentate ligands with different electron-withdrawing substituents. The two complexes are blue and orange solid-state fluorophores, respectively, highly responsive to thermal and mechanical stress. These emitters show a very different photoluminescent (PL) pattern as recorded before and after the annealing treatment. Through X-ray structural analysis combined with thermal analysis, infrared (IR) spectroscopy, PL, and DFT simulation we provide a comprehensive analysis of the structural feature involved in the fluorochromic response. Notably, we were able to correlate the on-off thermo-fluorochromism of the complexes with the structural rearrangement at the zinc coordination core. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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18 pages, 3608 KiB  
Article
A Water Soluble 2-Phenyl-5-(pyridin-3-yl)-1,3,4-oxadiazole Based Probe: Antimicrobial Activity and Colorimetric/Fluorescence pH Response
by Rosita Diana, Ugo Caruso, Luigi Di Costanzo, Simona Concilio, Stefano Piotto, Lucia Sessa and Barbara Panunzi
Molecules 2022, 27(6), 1824; https://doi.org/10.3390/molecules27061824 - 11 Mar 2022
Cited by 6 | Viewed by 2597
Abstract
The growing demand of responsive tools for biological and biomedical applications pushes towards new low-cost probes easy to synthesize and versatile. Current optical probes are theranostic tools simultaneously responsive to biological parameters/analyte and therapeutically operating. Among the optical methods for pH monitoring, simple [...] Read more.
The growing demand of responsive tools for biological and biomedical applications pushes towards new low-cost probes easy to synthesize and versatile. Current optical probes are theranostic tools simultaneously responsive to biological parameters/analyte and therapeutically operating. Among the optical methods for pH monitoring, simple small organic molecules including multifunctional probes for simultaneous biological activity being highly desired by scientists and technicians. Here, we present a novel pH-responsive probe with a three-ring heteroaromatic pattern and a flexible cationic chain. The novel molecule shows real-time naked-eye colorimetric and fluorescence response in the slightly acidic pH range besides its excellent solubility both in the organic phase and in water. In addition, the small probe shows significant antibacterial activity, particularly against Escherichia coli. Single-crystal X-ray study and density functional theory (DFT) calculations rationalize the molecule spectroscopic response. Finally, molecular dynamics (MD) elucidate the interactions between the probe and a model cell membrane. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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16 pages, 3391 KiB  
Article
Stability of Manganese(II)–Pyrazine, –Quinoxaline or –Phenazine Complexes and Their Potential as Carbonate Sequestration Agents
by José J. N. Segoviano-Garfias, Gabriela A. Zanor, Fidel Ávila-Ramos and Egla Yareth Bivián-Castro
Molecules 2022, 27(5), 1648; https://doi.org/10.3390/molecules27051648 - 2 Mar 2022
Cited by 2 | Viewed by 2906
Abstract
Carbonate sequestration technology is a complement of CO2 sequestration technology, which might assure its long-term viability. In this work, in order to explore the interactions between Mn2+ ion with several ligands and carbonate ion, we reported a spectrophotometric equilibrium study of [...] Read more.
Carbonate sequestration technology is a complement of CO2 sequestration technology, which might assure its long-term viability. In this work, in order to explore the interactions between Mn2+ ion with several ligands and carbonate ion, we reported a spectrophotometric equilibrium study of complexes of Mn2+ with pyrazine, quinoxaline or phenazine and its carbonate species at 298 K. For the complexes of manganese(II)–pyrazine, manganese(II)–quinoxaline and manganese(II)–phenazine, the formation constants obtained were log β110 = 4.6 ± 0.1, log β110 = 5.9 ± 0.1 and log β110 = 6.0 ± 0.1, respectively. The formation constants for the carbonated species manganese(II)–carbonate, manganese(II)–pyrazine–carbonate, manganese(II)–quinoxaline–carbonate and manganese(II)–phenazine–carbonate complexes were log β110 = 5.1 ± 0.1, log β110 = 9.8 ± 0.1, log β110 = 11.7 ± 0.1 and log β110 = 12.7 ± 0.1, respectively. Finally, the individual calculated electronic spectra and its distribution diagram of these species are also reported. The use of N-donor ligand with π-electron-attracting activity in a manganese(II) complex might increase its interaction with carbonate ions. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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18 pages, 3032 KiB  
Article
A Novel L-Shaped Fluorescent Probe for AIE Sensing of Zinc (II) Ion by a DR/NIR Response
by Rosita Diana, Ugo Caruso, Francesco Silvio Gentile, Luigi Di Costanzo and Barbara Panunzi
Molecules 2021, 26(23), 7347; https://doi.org/10.3390/molecules26237347 - 3 Dec 2021
Cited by 7 | Viewed by 2882
Abstract
In the field of optical sensors, small molecules responsive to metal cations are of current interest. Probes displaying aggregation-induced emission (AIE) can solve the problems due to the aggregation-caused quenching (ACQ) molecules, scarcely emissive as aggregates in aqueous media and in tissues. The [...] Read more.
In the field of optical sensors, small molecules responsive to metal cations are of current interest. Probes displaying aggregation-induced emission (AIE) can solve the problems due to the aggregation-caused quenching (ACQ) molecules, scarcely emissive as aggregates in aqueous media and in tissues. The addition of a metal cation to an AIE ligand dissolved in solution can cause a “turn-on” of the fluorescence emission. Half-cruciform-shaped molecules can be a winning strategy to build specific AIE probes. Herein, we report the synthesis and characterization of a novel L-shaped fluorophore containing a benzofuran core condensed with 3-hydroxy-2-naphthaldehyde crossed with a nitrobenzene moiety. The novel AIE probe produces a fast colorimetric and fluorescence response toward zinc (II) in both in neutral and basic conditions. Acting as a tridentate ligand, it produces a complex with enhanced and red-shifted emission in the DR/NIR spectral range. The AIE nature of both compounds was examined on the basis of X-ray crystallography and DFT analysis. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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Review

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34 pages, 13571 KiB  
Review
Recent Progress in Photoresponsive Biomaterials
by Miriam Di Martino, Lucia Sessa, Rosita Diana, Stefano Piotto and Simona Concilio
Molecules 2023, 28(9), 3712; https://doi.org/10.3390/molecules28093712 - 25 Apr 2023
Cited by 36 | Viewed by 5197
Abstract
Photoresponsive biomaterials have garnered increasing attention recently due to their ability to dynamically regulate biological interactions and cellular behaviors in response to light. This review provides an overview of recent advances in the design, synthesis, and applications of photoresponsive biomaterials, including photochromic molecules, [...] Read more.
Photoresponsive biomaterials have garnered increasing attention recently due to their ability to dynamically regulate biological interactions and cellular behaviors in response to light. This review provides an overview of recent advances in the design, synthesis, and applications of photoresponsive biomaterials, including photochromic molecules, photocleavable linkers, and photoreactive polymers. We highlight the various approaches used to control the photoresponsive behavior of these materials, including modulation of light intensity, wavelength, and duration. Additionally, we discuss the applications of photoresponsive biomaterials in various fields, including drug delivery, tissue engineering, biosensing, and optical storage. A selection of significant cutting-edge articles collected in recent years has been discussed based on the structural pattern and light-responsive performance, focusing mainly on the photoactivity of azobenzene, hydrazone, diarylethenes, and spiropyrans, and the design of smart materials as the most targeted and desirable application. Overall, this review highlights the potential of photoresponsive biomaterials to enable spatiotemporal control of biological processes and opens up exciting opportunities for developing advanced biomaterials with enhanced functionality. Full article
(This article belongs to the Special Issue Stimuli-Responsive Chromophores and Luminophores)
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