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Design, Synthesis, and Mechanism of Fluorescent and Luminescent Materials

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Materials Science".

Deadline for manuscript submissions: closed (31 May 2024) | Viewed by 6140

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Guest Editor
Physical Chemistry Department, University of the Basque Country (UPV/EHU), 48080 Bilbao, Spain
Interests: nano-objects and organic nanomaterials; nanostructures and nanoparticles (zeolites, latex nanoparticles); supramolecular chemistry; photonics and opto-electronics; photochemistry and photophysics; nano-photochemistry; microspectroscopy and fluorescence nano-imaging

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Physical Chemistry, Universidad del País Vasco / Euskal Herriko Unibertsitatea, UPV/EHU Apartado 644, 48080 Bilbao, Spain
Interests: photoactive hybrid zeolitic materials and nanoparticles for optoelectronics and biophotonics; self-assembled dyes as fluorescent and chiroptic organic materials
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

New types of fluorescence/luminiscent materials have been springing up in the last decades due to their potential applications in emerging areas suchs as modern organic electronics and solar energy conversion (OLEDs, organic photovoltaics, organic semiconductors), optical data storage, biotechnology (biomarkers, fluorescent sensors, anticancer treatments, quirooptics), and lasers among others. One of the biggest challenges for scientists consists in controlling the size, shape and structure of the emissive materials, which determines their physical and chemical properties and has a huge influence on their performances. Thus, mastering the synthesis process and understanding the relationship between the emission properties (fluorescence, bioluminescence, chemiluminescence, electroluminescence) and intermolecular/intramolecular interactions has become a hot research topic.

The aim of this special issue is to attract world-leading researchers in the area of organic/inorganic synthesis, materials science, physical chemistry and biochemistry to detail the state-of-the-art in the design and development of fluorescent and luminescent materials for a broad range of optoelectronic aplications. This Research Topic welcomes original research, review, and perspective articles covering a broad range of emissive materials, some examples listed bellow:

  1. Organic materials: dye-based nanomaterials, organic gels, supramolecular polymers, covalent oligomers.
  2. Inorganic materials: QDs (quantum dots), MNPs (metal nanoparticles), UCNPs (up-conversion nanoparticles), CDs (carbon dots), perovskites.
  3. Organic/inorganic hybrid materials: host/guest sytems, MOFs (metal-organic frameworks).

Dr. Leire Gartzia-Rivero
Dr. Jorge Bañuelos Prieto
Guest Editors

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Keywords

  • luminiscent materials
  • molecular design and synthesis
  • supramolecular chemistry
  • emissive mechanisms and processes
  • photophysics
  • photochemistry
  • probes and sensors
  • optoelectronics

Published Papers (5 papers)

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Research

14 pages, 2801 KiB  
Article
Confinement of a Styryl Dye into Nanoporous Aluminophosphates: Channels vs. Cavities
by Ainhoa Oliden-Sánchez, Rebeca Sola-Llano, Joaquín Pérez-Pariente, Luis Gómez-Hortigüela and Virginia Martínez-Martínez
Int. J. Mol. Sci. 2024, 25(7), 3577; https://doi.org/10.3390/ijms25073577 - 22 Mar 2024
Viewed by 544
Abstract
Styryl dyes are generally poor fluorescent molecules inherited from their flexible molecular structures. However, their emissive properties can be boosted by restricting their molecular motions. A tight confinement into inorganic molecular sieves is a good strategy to yield highly fluorescent hybrid systems. In [...] Read more.
Styryl dyes are generally poor fluorescent molecules inherited from their flexible molecular structures. However, their emissive properties can be boosted by restricting their molecular motions. A tight confinement into inorganic molecular sieves is a good strategy to yield highly fluorescent hybrid systems. In this work, we compare the confinement effect of two Mg-aluminophosphate zeotypes with distinct pore systems (the AEL framework, a one-dimensional channeled structure with elliptical pores of 6.5 Å × 4.0 Å, and the CHA framework, composed of large cavities of 6.7 Å × 10.0 Å connected by eight-ring narrower windows) for the encapsulation of 4-DASPI styryl dye (trans-4-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide). The resultant hybrid systems display significantly improved photophysical features compared to 4-DASPI in solution as a result of tight confinement in both host inorganic frameworks. Molecular simulations reveal a tighter confinement of 4-DASPI in the elliptical channels of AEL, explaining its excellent photophysical properties. On the other hand, a singular arrangement of 4-DASPI dye is found when confined within the cavity-based CHA framework, where the 4-DASPI molecule spans along two adjacent cavities, with each aromatic ring sitting on these adjacent cavities and the polymethine chain residing within the narrower eight-ring window. However, despite the singularity of this host–guest arrangement, it provides less tight confinement for 4-DASPI than AEL, resulting in a slightly lower quantum yield. Full article
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14 pages, 4126 KiB  
Article
Synthesis and Crystal Structure of the Europium(II) Hydride Oxide Iodide Eu5H2O2I4 Showing Blue-Green Luminescence
by Daniel Rudolph, Thomas Wylezich, Philip Netzsch, Björn Blaschkowski, Henning A. Höppe, Philippe Goldner, Nathalie Kunkel, Jean-Louis Hoslauer and Thomas Schleid
Int. J. Mol. Sci. 2023, 24(19), 14969; https://doi.org/10.3390/ijms241914969 - 7 Oct 2023
Viewed by 1077
Abstract
As the first europium(II) hydride oxide iodide, dark red single crystals of Eu5H2O2I4 could be synthesized from oxygen-contaminated mixtures of EuH2 and EuI2. Its orthorhombic crystal structure (a = 1636.97(9) pm, b [...] Read more.
As the first europium(II) hydride oxide iodide, dark red single crystals of Eu5H2O2I4 could be synthesized from oxygen-contaminated mixtures of EuH2 and EuI2. Its orthorhombic crystal structure (a = 1636.97(9) pm, b = 1369.54(8) pm, c = 604.36(4) pm, Z = 4) was determined via single-crystal X-ray diffraction in the space group Cmcm. Anion-centred tetrahedra [HEu4]7+ and [OEu4]6+ serve as central building blocks interconnected via common edges to infinite ribbons parallel to the c axis. These ribbons consist of four trans-edge connected (Eu2+)4 tetrahedra as repetition unit, two H-centred ones in the inner part, and two O2−-centred ones representing the outer sides. They are positively charged, according to 1{[Eu5H2O2]4+}, to become interconnected and charge-balanced by iodide anions. Upon excitation with UV light, the compound shows blue–green luminescence with the shortest Eu2+ emission wavelength ever observed for a hydride derivative, peaking at 463 nm. The magnetic susceptibility of Eu5H2O2I4 follows the Curie-Weiss law down to 100 K, and exhibits a ferromagnetic ordering transition at about 10 K. Full article
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13 pages, 5704 KiB  
Article
Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
by Carolina Díaz-Norambuena, Edurne Avellanal-Zaballa, Alejandro Prieto-Castañeda, Jorge Bañuelos, Santiago de la Moya, Antonia R. Agarrabeitia and María J. Ortiz
Int. J. Mol. Sci. 2023, 24(14), 11837; https://doi.org/10.3390/ijms241411837 - 23 Jul 2023
Viewed by 1125
Abstract
Heavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), respectively, with minimal side [...] Read more.
Heavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), respectively, with minimal side effects. In this regard, BODIPY-based orthogonal dimers have irrupted as suitable candidates for this aim. Herein, we analyse the photophysical properties of a set of formyl-functionalized BODIPY dimers to ascertain their suitability as fluorescent photosensitizers. The conducted computationally aided spectroscopic study determined that the fluorescence/singlet oxygen generation dual performance of these valuable BODIPY dimers not only depends on the BODIPY-BODIPY linkage and the steric hindrance around it, but also can be modulated by proper formyl functionalization at specific chromophoric positions. Thus, we propose regioselective formylation as an effective tool to modulate such a delicate photonic balance in BODIPY-based dimeric photosensitizers. The taming of the excited-state dynamics, in particular intramolecular charge transfer as the key underlying process mediating fluorescence deactivation vs. intersystem crossing increasing, could serve to increase fluorescence for brighter bioimaging, enhance the generation of singlet oxygen for killing activity, or balance both for photo-theragnosis. Full article
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12 pages, 3652 KiB  
Article
What Other Than Acridinium Esters? Computational Search for New Acridinium-Based Chemiluminogens
by Milena Pieńkos and Beata Zadykowicz
Int. J. Mol. Sci. 2023, 24(11), 9468; https://doi.org/10.3390/ijms24119468 - 30 May 2023
Cited by 1 | Viewed by 1159
Abstract
The rapid increase in disease prevalence in the world makes it extremely important to search for new or develop existing diagnostic methods, for example, chemiluminescent labeling used in immunodiagnostics. At present, acridinium esters are willingly used as chemiluminogenic fragments of labels. However, the [...] Read more.
The rapid increase in disease prevalence in the world makes it extremely important to search for new or develop existing diagnostic methods, for example, chemiluminescent labeling used in immunodiagnostics. At present, acridinium esters are willingly used as chemiluminogenic fragments of labels. However, the search for new chemiluminogens that are particularly efficient is the main task of our studies. The density functional theory (DFT) and time-dependent (TD) DFT methods were used to obtain thermodynamic and kinetic results concerning the chemiluminescence and competitive dark reactions, which indicated whether some of the scrutinized derivatives have better characteristics than the chemiluminogens used so far. Synthesis of these candidates for efficient chemiluminogens, followed by studies of their chemiluminescent properties, and ultimately in chemiluminescent labeling, are further steps to confirm their potential applicability in immunodiagnostics. Full article
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19 pages, 5631 KiB  
Article
Preparation and Optical Study of 1-Formamido-5-Isocyanonaphthalene, the Hydrolysis Product of the Potent Antifungal 1,5-Diisocyanonaphthalene
by Erika Kopcsik, Zoltán Mucsi, Bence Kontra, László Vanyorek, Csaba Váradi, Béla Viskolcz and Miklós Nagy
Int. J. Mol. Sci. 2023, 24(9), 7780; https://doi.org/10.3390/ijms24097780 - 24 Apr 2023
Viewed by 1693
Abstract
Aromatic isocyanides have gained a lot of attention lately as promising antifungal and anticancer drugs, as well as high-performance fluorescent analytical probes for the detection of toxic metals, such as mercury, even in vivo. Since this topic is relatively new and aromatic isocyanides [...] Read more.
Aromatic isocyanides have gained a lot of attention lately as promising antifungal and anticancer drugs, as well as high-performance fluorescent analytical probes for the detection of toxic metals, such as mercury, even in vivo. Since this topic is relatively new and aromatic isocyanides possess unique photophysical properties, the understanding of structure–behavior relationships and the preparation of novel potentially biologically active derivatives are of paramount importance. Here, we report the photophysical characterization of 1,5-diisocyanonaphthalene (DIN) backed by quantum chemical calculations. It was discovered that DIN undergoes hydrolysis in certain solvents in the presence of oxonium ions. By the careful control of the reaction conditions for the first time, the nonsymmetric product 1-formamido-5-isocyanonaphthalene (ICNF) could be prepared. Contrary to expectations, the monoformamido derivative showed a significant solvatochromic behavior with a ~50 nm range from hexane to water. This behavior was explained by the enhanced H-bond-forming ability of the formamide group. The significance of the hydrolysis reaction is that the isocyano group is converted to formamide in living organisms. Therefore, ICNF could be a potential drug (for example, antifungal) and the reaction can be used as a model for the preparation of other nonsymmetric formamido–isocyanoarenes. In contrast to its relative 1-amino-5-iscyanonaphthalene (ICAN), ICNF is highly fluorescent in water, enabling the development of a fluorescent turnoff probe. Full article
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