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Lumino and Fluorophores—Illuminating Science and Technology
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Lumino and Fluorophores—Illuminating Science and Technology

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

Deadline for manuscript submissions: closed (31 May 2019) | Viewed by 52711

Special Issue Editors

Dr. Gregor Drummen

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Guest Editor
Cellular Stress and Ageing Program, Bionanoscience and Bioimaging Program, BNS, 33647 Bielefeld, Germany
Interests: quantum dots; bionanotechnology; two-photon fluorescence imaging; cellular imaging; fluorescence microscopy; cancer; cell signaling; oxidative stress; lipids and biomembranes; lipid peroxidation; antioxidants; renal pathobiology; extracellular vesicles; Super-resolution microscopy
Special Issues, Collections and Topics in MDPI journals
Dr. Hellen Ishikawa-Ankerhold

E-Mail Website
Guest Editor
Walter Brendel Centre of Experimental Medicine, Department of Cardiology, Ludwig Maximilian University of Munich, Marchioninistraße 27, D-81377 München, Germany
Interests: multiphoton microscopy; intravital microscopy; confocal and super-resolution microscopy; fluorescent probes; leukocyte trafficking; atherosclerosis; inflammation; hematopoiesis and cytoskeleton proteins
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Ever since the invention of lenses, man has, not only looked into the skies, but also into the realm of the invisible microscopic world of tissues, cells, and micro-organisms. The use of fluorescent labels and the development of various forms of optical microscopy, in particular confocal laser scanning microscopy (CLSM), have significantly advanced our knowledge about the basic mechanisms underpinning biology and the pathophysiological processes that lead to disease. Furthermore, fluorescence-based assays have largely replaced radioactive assays in the lab. In addition, luminescent compounds and particles have enriched various technologies, including display technology, optoelectronics, solar devices, and optical storage.

It is intended that this Special Issue will consider fundamental physicochemical properties, synthesis and modification, biomedical, imaging and assay applications of luminescent compounds and fluorophores, from organic dyes to fluorescent nanoparticles and fluorescent proteins. In this respect, it should be stressed that the luminescent/fluorescent compound always takes centre stage. Previously unpublished experimental, theoretical, prospective, historical, and review papers are solicited on the related topics.

Dr. Gregor Drummen
Dr. Hellen Ishikawa-Ankerhold
Guest Editors

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Keywords

  • Synthesis and modification of fluorophores
  • Physico-chemical and fluorescent properties
  • Biocompatibility and cytotoxicity
  • Live-cell tracking and imaging
  • Whole animal imaging
  • FRET, FLIM, FRAP, FLIP et al
  • Applications in cell biology and (bio)medicine
  • Fluorescence-based assays and biosensors
  • Nanotechnology
  • Optoelectronics
  • Solar devices

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Published Papers (12 papers)

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Research

11 pages, 3466 KiB  
Article
Solid State Room Temperature Dual Phosphorescence from 3-(2-Fluoropyridin-4-yl)triimidazo[1,2-a:1′,2′-c:1″,2″-e][1,3,5]triazine
by Andrea Previtali, Elena Lucenti, Alessandra Forni, Luca Mauri, Chiara Botta, Clelia Giannini, Daniele Malpicci, Daniele Marinotto, Stefania Righetto and Elena Cariati
Molecules 2019, 24(14), 2552; https://doi.org/10.3390/molecules24142552 - 13 Jul 2019
Cited by 19 | Viewed by 3493
Abstract
Organic room temperature persistent luminescence is a fascinating but still largely unexplored phenomenon. Cyclic-triimidazole and its halogenated (Br, I) derivatives have recently revealed as intriguing phosphors characterized by multifaceted emissive behavior including room temperature ultralong phosphorescence (RTUP) associated with the presence of H-aggregates [...] Read more.
Organic room temperature persistent luminescence is a fascinating but still largely unexplored phenomenon. Cyclic-triimidazole and its halogenated (Br, I) derivatives have recently revealed as intriguing phosphors characterized by multifaceted emissive behavior including room temperature ultralong phosphorescence (RTUP) associated with the presence of H-aggregates in their crystal structure. Here, we move towards a multicomponent system by incorporating a fluoropyridinic fragment on the cyclic-triimidazole scaffold. Such chromophore enhances the molecular properties resulting in a high photoluminescence quantum yield (PL QY) in solution but preserves the solid-state RTUP. By means of X-ray diffraction (XRD) analysis, theoretical calculations, steady-state and time-resolved spectroscopy on solutions, polymethylmethacrylate (PMMA) blends and crystals, the nature of the different radiative deactivation channels of the compound has been disclosed. In particular, the molecular fluorescence and phosphorescence, this latter observed in frozen solution and in PMMA blends, are associated to deactivation from S1 and T1 respectively, while the low energy RTUP, observed only for crystals, is interpreted as originated from H aggregates. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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15 pages, 3799 KiB  
Article
Effect of the Substitution Position on the Electronic and Solvatochromic Properties of Isocyanoaminonaphthalene (ICAN) Fluorophores
by Sándor Lajos Kovács, Miklós Nagy, Péter Pál Fehér, Miklós Zsuga and Sándor Kéki
Molecules 2019, 24(13), 2434; https://doi.org/10.3390/molecules24132434 - 2 Jul 2019
Cited by 9 | Viewed by 3463
Abstract
The properties of 1,4-isocyanoaminonaphthalene (1,4-ICAN) and 2,6-isocyanoaminonaphthalene (2,6-ICAN) isomers are discussed in comparison with those of 1,5-isocyanoaminonaphthalene (1,5-ICAN), which exhibits a large positive solvatochromic shift similar to that of Prodan. In these isocyanoaminonaphthalene derivatives, the isocyano and the amine group serve as the [...] Read more.
The properties of 1,4-isocyanoaminonaphthalene (1,4-ICAN) and 2,6-isocyanoaminonaphthalene (2,6-ICAN) isomers are discussed in comparison with those of 1,5-isocyanoaminonaphthalene (1,5-ICAN), which exhibits a large positive solvatochromic shift similar to that of Prodan. In these isocyanoaminonaphthalene derivatives, the isocyano and the amine group serve as the donor and acceptor moieties, respectively. It was found that the positions of the donor and the acceptor groups in these naphthalene derivatives greatly influence the Stokes and solvatochromic shifts, which decrease in the following order: 1,5-ICAN > 2,6-ICAN > 1,4-ICAN. According to high-level quantum chemical calculations, this order is well correlated with the charge transfer character of these compounds upon excitation. Furthermore, unlike 1,5-ICAN, the 1,4-ICAN and 2,6-ICAN isomers showed relatively high quantum yields in water, that were determined to be 0.62 and 0.21, respectively. In addition, time-resolved fluorescence experiments revealed that both the radiative and non-radiative decay rates for these three ICAN isomers varied unusually with the solvent polarity parameter ET(30). The explanations of the influence of the solvent polarity on the resulting steady-state and time-resolved fluorescence emission spectra are also discussed. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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16 pages, 1826 KiB  
Article
Emissive Enhancement of the Singlet Oxygen Chemiluminescence Probe after Binding to Bovine Serum Albumin
by Jon Miranda-Apodaca, Nir Hananya, Adrián Velázquez-Campoy, Doron Shabat and Juan B. Arellano
Molecules 2019, 24(13), 2422; https://doi.org/10.3390/molecules24132422 - 1 Jul 2019
Cited by 10 | Viewed by 4319
Abstract
A chemiluminescence probe for singlet oxygen 1O2 (SOCL) was investigated in phosphate buffer saline (PBS), either in the absence of proteins or containing bovine serum albumin (BSA). In the protein-free PBS, the reactivity of SOCL for methylene blue (MB)-photosensitized 1O [...] Read more.
A chemiluminescence probe for singlet oxygen 1O2 (SOCL) was investigated in phosphate buffer saline (PBS), either in the absence of proteins or containing bovine serum albumin (BSA). In the protein-free PBS, the reactivity of SOCL for methylene blue (MB)-photosensitized 1O2 was found to be moderate or low. The reaction yield increased with temperature and/or concentration of dissolved molecular oxygen. Unexpectedly, the presence of BSA boosted both the emissive nature and the thermal stability of the phenoxy-dioxetane intermediate formed in the chemiexcitation pathway. Isothermal titration calorimetry showed that SOCL has a moderate binding affinity for BSA and that entropy forces drive the formation of the SOCL-BSA complex. A model with two identical and independent binding sites was used to fit the binding isotherm data. Co-operative binding was observed when MB was present. Local viscosity factors and/or conformational restrictions of the BSA-bound SOCL phenoxy-dioxetane were proposed to contribute to the formation of the highly emissive benzoate ester during the chemically initiated electron exchange luminescence (CIEEL) process. These results led us to conclude that hydrophobic interactions of the SOCL with proteins can modify the emissive nature of its phenoxy-dioxetane, which should be taken into account when using SOCL or its cell-penetrating peptide derivative in living cells. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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12 pages, 2281 KiB  
Article
The Physical Vapor Transport Method for Bulk AlN Crystal Growth
by Wen-Hao Chen, Zuo-Yan Qin, Xu-Yong Tian, Xu-Hui Zhong, Zhen-Hua Sun, Bai-Kui Li, Rui-Sheng Zheng, Yuan Guo and Hong-Lei Wu
Molecules 2019, 24(8), 1562; https://doi.org/10.3390/molecules24081562 - 19 Apr 2019
Cited by 27 | Viewed by 5431
Abstract
In this report, the development of physical vapor transport (PVT) methods for bulk aluminum nitride (AlN) crystal growth is reviewed. Three modified PVT methods with different features including selected growth at a conical zone, freestanding growth on a perforated sheet, and nucleation control [...] Read more.
In this report, the development of physical vapor transport (PVT) methods for bulk aluminum nitride (AlN) crystal growth is reviewed. Three modified PVT methods with different features including selected growth at a conical zone, freestanding growth on a perforated sheet, and nucleation control with an inverse temperature gradient are discussed and compared in terms of the size and quality of the bulk AlN crystals they can produce as well as the process complexity. The PVT method with an inverse temperature gradient is able to significantly reduce the nucleation rate and realize the dominant growth of only one bulk AlN single crystal, and thus grow centimeter-sized bulk AlN single crystals. X-ray rocking curve (XRC) and Raman spectroscopy measurements showed a high crystalline quality of the prepared AlN crystals. The inverse temperature gradient provides an efficient and relatively low-cost method for the preparation of large-sized and high-quality AlN seed crystals used for seeded growth, devoted to the diameter enlargement and quality improvement of bulk AlN single crystals. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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10 pages, 2837 KiB  
Article
Triboluminescence of Centrosymmetric Lanthanide β-Diketonate Complexes with Aggregation-Induced Emission
by Ho-Yin Wong, Wesley Ting Kwok Chan and Ga-Lai Law
Molecules 2019, 24(4), 662; https://doi.org/10.3390/molecules24040662 - 13 Feb 2019
Cited by 14 | Viewed by 4094
Abstract
Triboluminescence (TL) is a form of light emission induced upon mechanical forces on the material. However, our understanding of this phenomenon is still unclear and more examples are therefore needed in order to elucidate its mechanism. In this work, two types of TL [...] Read more.
Triboluminescence (TL) is a form of light emission induced upon mechanical forces on the material. However, our understanding of this phenomenon is still unclear and more examples are therefore needed in order to elucidate its mechanism. In this work, two types of TL complexes, [Eu(pp-dbm-Cl2)3phen] and [Eu(mm-dbm-Cl2)3phen], which also displays aggregation-induced emission (AIE) were synthesized and investigated for its photo-physical and crystal structural properties. These complexes were crystallized in a centro-symmetric space group P21/n, and remarkably, displayed TL upon grinding that may be due to the presence of extensive π···π, C-H···π and C-H···Cl-C interactions in the close molecular packing of its structure. This rare example deviates from the widely accepted mechanism of TL, hence widening the scope of our understanding in the area. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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10 pages, 3991 KiB  
Article
Mechanoresponsive Material of AIE-Active 1,4-Dihydropyrrolo[3,2-b]pyrrole Luminophores Bearing Tetraphenylethylene Group with Rewritable Data Storage
by Yuqing Ma, Yuyang Zhang, Lin Kong and Jiaxiang Yang
Molecules 2018, 23(12), 3255; https://doi.org/10.3390/molecules23123255 - 10 Dec 2018
Cited by 21 | Viewed by 4547
Abstract
A new tetraphenylethylene (TPE) functionalized 1,4-dihydropyrrolo[3,2-b]pyrrole derivative (APPTPECN) was synthesized with obvious aggregation-induced emission (AIE) active by simple synthetic method. APPTPECN exhibited reversible mechanofluorochromic (MFC) behavior. The powder X-ray diffraction (PXRD) and scanning electron microscopy (SEM) investigations exhibited that [...] Read more.
A new tetraphenylethylene (TPE) functionalized 1,4-dihydropyrrolo[3,2-b]pyrrole derivative (APPTPECN) was synthesized with obvious aggregation-induced emission (AIE) active by simple synthetic method. APPTPECN exhibited reversible mechanofluorochromic (MFC) behavior. The powder X-ray diffraction (PXRD) and scanning electron microscopy (SEM) investigations exhibited that the MFC nature is originated through a conversion from the microcrystalline to amorphous phase under the stimulus of external force. The results obtained would be of major help in understanding the MFC mechanism and designing new MFC materials. Compound APPTPECN has the potential possibility to employ in rewritable data storage and is of assistance in the rational design of smart luminescent materials. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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11 pages, 1389 KiB  
Article
Design of Novel Pyrene-Bodipy Dyads: Synthesis, Characterization, Optical Properties, and FRET Studies
by Pasquale Porcu, Mireille Vonlanthen, Israel González-Méndez, Andrea Ruiu and Ernesto Rivera
Molecules 2018, 23(9), 2289; https://doi.org/10.3390/molecules23092289 - 7 Sep 2018
Cited by 16 | Viewed by 5032
Abstract
A new series of dendronized bodipys containing pyrene units was synthesized and characterized. Their optical and photophysical properties were determined by absorption and fluorescence spectroscopy. This series includes three different compounds. The first one has an anisole group linked to the bodipy unit, [...] Read more.
A new series of dendronized bodipys containing pyrene units was synthesized and characterized. Their optical and photophysical properties were determined by absorption and fluorescence spectroscopy. This series includes three different compounds. The first one has an anisole group linked to the bodipy unit, which was used as the reference compound. In the second, the bodipy core is linked to a zero generation dendron with one pyrene unit. The third compound contains a first generation Fréchet-type dendron bearing two pyrene units. In this work, the combination pyrene-bodipy was selected as the donor-acceptor pair for this fluorescence resonance energy transfer (FRET) study. Doubtless, these two chromophores exhibit high quantum yields, high extinction coefficients, and both their excitation and emission wavelengths are located in the visible region. This report presents a FRET study of a novel series of pyrene-bodipy dendritic molecules bearing flexible spacers. We demonstrated via spectroscopic studies that FRET phenomena occur in these dyads. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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14 pages, 3442 KiB  
Article
AIE/ACQ Effects in Two DR/NIR Emitters: A Structural and DFT Comparative Analysis
by Ugo Caruso, Barbara Panunzi, Rosita Diana, Simona Concilio, Lucia Sessa, Rafi Shikler, Shiran Nabha, Angela Tuzi and Stefano Piotto
Molecules 2018, 23(8), 1947; https://doi.org/10.3390/molecules23081947 - 4 Aug 2018
Cited by 39 | Viewed by 4979
Abstract
The effects of aggregation-induced emission (AIE) and of aggregation caused quenching (ACQ) were observed and discussed on two solid materials based on a phenylenevinylene (PV) and a dicyano-PV structure. The brightest emitter in solid films shows a high fluorescence quantum yield in the [...] Read more.
The effects of aggregation-induced emission (AIE) and of aggregation caused quenching (ACQ) were observed and discussed on two solid materials based on a phenylenevinylene (PV) and a dicyano-PV structure. The brightest emitter in solid films shows a high fluorescence quantum yield in the deep red/near IR (DR/NIR) region (75%). The spectroscopic properties of the two crystalline solids have been described and compared in terms of crystallographic data and time dependent DFT analysis. The influence of the cyano-substituents on AIE/ACQ mechanism activation was discussed. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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8 pages, 1168 KiB  
Communication
A Self-Assembled ZnII-NdIII Heterohexanuclear Dimer Based on a Hexadentate N2O4-Type Ligand and Terephthalic Acid: Synthesis, Structure, and Fluorescence Properties
by Li-Jun Ru, Lei Gao, Wen-Ting Guo, Jian-Chun Ma and Wen-Kui Dong
Molecules 2018, 23(7), 1609; https://doi.org/10.3390/molecules23071609 - 2 Jul 2018
Cited by 1 | Viewed by 2958
Abstract
A self-assembled ZnII-NdIII heterohexanuclear coordination compound [Zn4Nd2(L)4(bdc)2]·2NO3 based on a hexadentate Salamo-like chelating ligand (H2L = 1,2-bis(3-methoxysalicylideneaminooxy)ethane]) and H2bdc (H2bdc = terephthalic acid) has been [...] Read more.
A self-assembled ZnII-NdIII heterohexanuclear coordination compound [Zn4Nd2(L)4(bdc)2]·2NO3 based on a hexadentate Salamo-like chelating ligand (H2L = 1,2-bis(3-methoxysalicylideneaminooxy)ethane]) and H2bdc (H2bdc = terephthalic acid) has been synthesized and characterized by elemental analyses, IR and UV/Vis spectra, and X-ray crystallography. Two crystallographically equivalent [Zn2Nd(L)2] moieties lie in the inversion center linked by two (bdc)2− ligands leading to a heterohexanuclear dimer in which the carboxylato group bridges the ZnII and NdIII atoms. The heteropolynuclear 3d-4f coordination compound includes four ZnII atoms, two NdIII atoms, four completely deprotonated (L)2− units, two fully deprotonated (bdc)2− units, and two crystalling nitrate ions. All of the ZnII atoms in the ZnII-NdIII coordination compound possess trigonal bipyramidal geometries and the NdIII atoms possess distorted bicapped square antiprism coordination arrangements. In addition, the fluorescence properties of the ligand and the ZnII-NdIII coordination compound were investigated. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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13 pages, 3463 KiB  
Article
Solid-State Highly Efficient DR Mono and Poly-dicyano-phenylenevinylene Fluorophores
by Barbara Panunzi, Rosita Diana, Simona Concilio, Lucia Sessa, Rafi Shikler, Shiran Nabha, Angela Tuzi, Ugo Caruso and Stefano Piotto
Molecules 2018, 23(7), 1505; https://doi.org/10.3390/molecules23071505 - 21 Jun 2018
Cited by 30 | Viewed by 4395
Abstract
An efficient deep red (DR)-emitting organic solid based on a dicyano-phenylenevinylene derivative was reported. The structural and spectroscopic properties of the solid have been described in terms of crystallographic data and time-dependent DFT analysis. A noteworthy fluorescence quantum yield of 53% was observed [...] Read more.
An efficient deep red (DR)-emitting organic solid based on a dicyano-phenylenevinylene derivative was reported. The structural and spectroscopic properties of the solid have been described in terms of crystallographic data and time-dependent DFT analysis. A noteworthy fluorescence quantum yield of 53% was observed for the brightest emitter cast into solid films. This result can be explained in terms of the aggregation-induced emission (AIE) effect. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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15 pages, 4443 KiB  
Article
Unprecedented Fluorescent Dinuclear CoII and ZnII Coordination Compounds with a Symmetric Bis(salamo)-Like Tetraoxime
by Lin-Wei Zhang, Ling-Zhi Liu, Fei Wang and Wen-Kui Dong
Molecules 2018, 23(5), 1141; https://doi.org/10.3390/molecules23051141 - 10 May 2018
Cited by 45 | Viewed by 4557
Abstract
Two unprecedented homometallic CoII and ZnII coordination compounds, [M2(L)(OCH3)][M2(L)(OAc)] (MII = CoII (1) and ZnII (2)), with a novel symmetric bis(salamo)-like tetraoxime ligand H3L were synthesized [...] Read more.
Two unprecedented homometallic CoII and ZnII coordination compounds, [M2(L)(OCH3)][M2(L)(OAc)] (MII = CoII (1) and ZnII (2)), with a novel symmetric bis(salamo)-like tetraoxime ligand H3L were synthesized and characterized by elemental analyses, infrafred (IR), ultraviolet–visible spectroscopy (UV-Vis), fluorescent spectra and single-crystal X-ray diffraction analyses. The unit cell of the two coordination compounds contains two crystallographically and chemically independent dinuclear coordination compounds. In the two coordination compounds, three metal ions are five-coordinated, formed two square pyramidal and a trigonal bipyramidal geometries, and the other metal ion is a hexacoordinate octahedral configuration. In addition, the coordination compound 1 forms a 3D supramolecular structure, and the coordination compound 2 forms a 0D dimer structure by the inter-molecular hydrogen bond interactions. Meanwhile, the fluorescence spectra of the coordination compounds 1 and 2 were also measured and discussed. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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14 pages, 2346 KiB  
Article
Synthesis and Fluorescence Properties of Structurally Characterized Heterobimetalic Cu(II)–Na(I) Bis(salamo)-Based Complex Bearing Square Planar, Square Pyramid and Triangular Prism Geometries of Metal Centers
by Xiu-Yan Dong, Qing Zhao, Zhi-Li Wei, Hao-Ran Mu, Han Zhang and Wen-Kui Dong
Molecules 2018, 23(5), 1006; https://doi.org/10.3390/molecules23051006 - 25 Apr 2018
Cited by 34 | Viewed by 4505
Abstract
A novel heterotrinuclear complex [Cu2(L)Na(µ-NO3)]∙CH3OH∙CHCl3 derived from a symmetric bis(salamo)-type tetraoxime H4L having a naphthalenediol unit, was prepared and structurally characterized via means of elemental analyses, UV-Vis, FT-IR, fluorescent spectra and single-crystal [...] Read more.
A novel heterotrinuclear complex [Cu2(L)Na(µ-NO3)]∙CH3OH∙CHCl3 derived from a symmetric bis(salamo)-type tetraoxime H4L having a naphthalenediol unit, was prepared and structurally characterized via means of elemental analyses, UV-Vis, FT-IR, fluorescent spectra and single-crystal X-ray diffraction. The heterobimetallic Cu(II)–Na(I) complex was acquired via the reaction of H4L with 2 equivalents of Cu(NO3)2·2H2O and 1 equivalent of NaOAc. Clearly, the heterotrinuclear Cu(II)–Na(I) complex has a 1:2:1 ligand-to-metal (Cu(II) and Na(I)) ratio. X-ray diffraction results exhibited the different geometric behaviors of the Na(I) and Cu(II) atoms in the heterotrinuclear complex; the both Cu(II) atoms are sited in the N2O2 coordination environments of fully deprotonated (L)4− unit. One Cu(II) atom (Cu1) is five-coordinated and possesses a geometry of slightly distorted square pyramid, while another Cu(II) atom (Cu2) is four-coordination possessing a square planar coordination geometry. Moreover, the Na(I) atom is in the O6 cavity and adopts seven-coordination with a geometry of slightly distorted single triangular prism. In addition, there are abundant supramolecular interactions in the Cu(II)–Na(I) complex. The fluorescence spectra showed the Cu(II)–Na(I) complex possesses a significant fluorescent quenching and exhibited a hypsochromic-shift compared with the ligand H4L. Full article
(This article belongs to the Special Issue Lumino and Fluorophores—Illuminating Science and Technology)
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