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Crystals
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Structure and Properties of Organic Dyes in Solid State
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Structure and Properties of Organic Dyes in Solid State

A special issue of Crystals (ISSN 2073-4352). This special issue belongs to the section "Organic Crystalline Materials".

Deadline for manuscript submissions: closed (30 June 2020) | Viewed by 23086

Special Issue Editor

Dr. Claudia Graiff

E-Mail Website
Guest Editor
Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, 43124 Parma, Italy
Interests: functional nanostructured materials; material characterization; photocatalysis; wastewater remediation; structural and solid-state characterization; cellulose nanocrystals
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Color, which is part of the beauty of Nature, is important for the attractiveness and acceptability of most products used in our society.

According to the literature, organic dyes and pigments show color because they (i) have at least one chromophore, (ii) possess a conjugated system with resonance of electrons, and (iii) absorb radiation in the visible spectrum; when these characteristics are lacking from the molecular structure, the color is lost.

Most of the physical and chemical properties of dyes (spectroscopic, surface, solution or solid state characteristics), the physical aspects of their preparation (precipitation, nucleation and growth, crystal formation), their photochemical or biological properties, and the relationship between color and chemical constitution cannot be fully understood if their crystal structure is not elucidated.

Recently ,organic dyes have been discovered as promising semiconducting materials, thanks to the formation of interactions between dyes and appropriate different semiconducting substrates; encapsulation and subsequent stabilization of organic dye into inorganic layered structures or MOF is also of interest because these systems often show a clear enhancement of the structural stability in temperature, indicating that the assembly may appear as a mutual benefit.

In all these cases, the full elucidation of solid state structure is of crucial importance in order to understand the adsorption and desorption mechanism with substrates. The main adsorption forces include electrostatic interaction, ion exchange, π–π complexation, and hydrogen bonds.

The chemistry of dyes, pigments, and their intermediates are of interest in diverse fields of activity such as cosmetics, reprographics, additives, medical research, polymers, etc.

This Special Issue of Crystals is designed as a collection of papers covering the broad field of investigation of the structure and properties of organic dyes in the solid state that appear as such or crystallized or co-crystallized with any types of substrates.

Prof. Dr. Claudia Graiff
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Crystals is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2100 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

  • organic dyes
  • solid state
  • crystallography
  • weak interactions
  • crystal packing
  • co-crystals
  • MOF

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Published Papers (5 papers)

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Editorial

Jump to: Research, Review

2 pages, 161 KiB  
Editorial
Structure and Properties of Organic Dyes in Solid State
by Claudia Graiff
Crystals 2020, 10(11), 1021; https://doi.org/10.3390/cryst10111021 - 9 Nov 2020
Cited by 1 | Viewed by 2004
Abstract
Color is one of the most fascinating aspects of Nature; it is part of the beauty of the environment that surrounds us, playing a key role in the acceptability of most products used in our society [...] Full article
(This article belongs to the Special Issue Structure and Properties of Organic Dyes in Solid State)

Research

Jump to: Editorial, Review

17 pages, 7614 KiB  
Article
Monosulfonated Azo Dyes: A Crystallographic Study of the Molecular Structures of the Free Acid, Anionic and Dianionic Forms
by Alan R. Kennedy, Linda K. Conway, Jennifer B. A. Kirkhouse, Karen M. McCarney, Olivier Puissegur, Edward Staunton, Simon J. Teat and John E. Warren
Crystals 2020, 10(8), 662; https://doi.org/10.3390/cryst10080662 - 1 Aug 2020
Cited by 14 | Viewed by 4032
Abstract
Crystallographic studies of monosulfonated azo dyes have concentrated on the salt forms that contain the azo anion. Here we present a study that compares the structures of these anions with protonated free acid forms and with doubly deprotonated dianion forms. To this end, [...] Read more.
Crystallographic studies of monosulfonated azo dyes have concentrated on the salt forms that contain the azo anion. Here we present a study that compares the structures of these anions with protonated free acid forms and with doubly deprotonated dianion forms. To this end, the new single crystal diffraction structures of 13 systematically related free acid forms of monosulfonated azo dyes are presented, together with three new structures of doubly deprotonated forms and two new structures of Na salt forms of azo anions. No structures of dideprotonated monosulfonated azo dyes have previously been reported and this paper also reports the first crystal structure of an azo dye with a hydronium cation. The geometries of the free acid, anion and dianion forms are compared to literature equivalents. It is shown that protonation of the azo bond gives predictable bond lengthening and shortening, which is of a greater magnitude than similar effects caused by azo-hydrazone tautomerisation, or the smaller again effects caused by the resonance electron donation from O or N based substituents. The dianion containing structures have twisted dianion geometries that can be understood based on the resonance effects of the phenoxide groups and upon the needs to bond to a relatively high number of metal cations. Full article
(This article belongs to the Special Issue Structure and Properties of Organic Dyes in Solid State)
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11 pages, 2907 KiB  
Article
The Design Strategy for an Aggregation- and Crystallization-Induced Emission-Active Molecule Based on the Introduction of Skeletal Distortion by Boron Complexation with a Tridentate Ligand
by Shunsuke Ohtani, Masayuki Gon, Kazuo Tanaka and Yoshiki Chujo
Crystals 2020, 10(7), 615; https://doi.org/10.3390/cryst10070615 - 15 Jul 2020
Cited by 28 | Viewed by 3757
Abstract
We describe here a new design strategy for obtaining boron complexes with aggregation- and crystallization-induced emission (AIE and CIE, respectively) properties based on the introduction of skeletal distortion. According to our recent results, despite the fact that an almost planar structure and robust [...] Read more.
We describe here a new design strategy for obtaining boron complexes with aggregation- and crystallization-induced emission (AIE and CIE, respectively) properties based on the introduction of skeletal distortion. According to our recent results, despite the fact that an almost planar structure and robust conjugation were obtained, the boron azomethine complex provided a slight emission in solution and an enhanced emission in aggregation and crystal. Quantum calculation results propose that unexpected emission annihilation in solution could be caused through intramolecular bending in the excited state. Herein, to realize this unique molecular motion and obtain AIE and CIE molecules, the phenyl quinoline-based boron complexes BPhQ and BPhQm with distorted and planar structures were designed and synthesized, respectively. BPhQm showed emission in solution and aggregation-caused quenching (ACQ, BPhQm: ΦF,sol. = 0.21, ΦF,agg. = 0.072, ΦF,cryst. = 0.051), while BPhQ exhibited a typical AIE and CIE (BPhQ: ΦF,sol. = 0.008, ΦF,agg. = 0.014, ΦF,cryst. = 0.017). The optical data suggest that a large degree of molecular motion should occur in BPhQ after photo-excitation because of the intrinsic skeletal distortion. Furthermore, single-crystal X-ray diffraction data indicate that the distorted π-conjugated system plays a positive role in presenting solid-state emission by inhibiting consecutive π–π interactions. We demonstrate in this paper that the introduction of the distorted structure by boron complexation should be a new strategy for realizing AIE and CIE properties. Full article
(This article belongs to the Special Issue Structure and Properties of Organic Dyes in Solid State)
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17 pages, 3270 KiB  
Article
Performance Comparison of Eichhornia crassipes and Salvinia natans on Azo-Dye (Eriochrome Black T) Phytoremediation
by Eszter Rápó, Katalin Posta, Alexandra Csavdári, Boglárka Éva Vincze, Gyöngyvér Mara, Gábor Kovács, Imane Haddidi and Szende Tonk
Crystals 2020, 10(7), 565; https://doi.org/10.3390/cryst10070565 - 1 Jul 2020
Cited by 23 | Viewed by 4670
Abstract
Organic pollutants, such as dyes, have a negative effect on the aqueous environment, therefore, their elimination from water bodies is a high priority. In this work, Eichhornia crassipes and Salvinia natans, both model plants with high phytoremediation efficiency, were exposed to various [...] Read more.
Organic pollutants, such as dyes, have a negative effect on the aqueous environment, therefore, their elimination from water bodies is a high priority. In this work, Eichhornia crassipes and Salvinia natans, both model plants with high phytoremediation efficiency, were exposed to various concentrations (Ci = 50–500 mg/L) of Eriochrome Black T (EBT). Their capacity to assimilate EBT was studied for 16 days of exposure, similar to natural conditions and by spectrophotometric monitoring of the dye concentration (EE. crassipes; 150 mg/L = 33%; ES. natans; 150 mg/L = 71.5%). The changes of the experimental parameters (pH—equalised by day 5, temperature, humidity, light intensity) were followed, and plant growth and biochemical responses to toxic stress effects (photosynthetic pigments, Energy-dispersive X-ray spectroscopy (EDX)—decreased effect of P, Mg, Ca, S and K, Scanning electron microscopy (SEM), defense enzyme) were examined. Furthermore, changes in oxidative- and photo-degradation of EBT in time and the solid-state properties (SEM, EDX, Fourier-transform infrared spectroscopy-FTIR) of the dye were investigated. Our results demonstrate that, despite the toxic stress, both species succeeded in reducing the dye-concentration of the water and S. natans proved to be more efficient in binding and removing organic dyes. With our findings, we proved that both plants alleviated the abiotic stress of dye contamination. Full article
(This article belongs to the Special Issue Structure and Properties of Organic Dyes in Solid State)
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Review

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43 pages, 8172 KiB  
Review
Fluorescence Phenomena in Amyloid and Amyloidogenic Bionanostructures
by B. Apter, N. Lapshina, H. Barhom, B. Fainberg, A. Handelman, A. Accardo, C. Diaferia, P. Ginzburg, G. Morelli and G. Rosenman
Crystals 2020, 10(8), 668; https://doi.org/10.3390/cryst10080668 - 3 Aug 2020
Cited by 23 | Viewed by 6786
Abstract
Nanoscale optical labeling is an advanced bioimaging tool. It is mostly based on fluorescence (FL) phenomena and enables the visualization of single biocells, bacteria, viruses, and biological tissues, providing monitoring of functional biosystems in vitro and in vivo, and the imaging-guided transportation of [...] Read more.
Nanoscale optical labeling is an advanced bioimaging tool. It is mostly based on fluorescence (FL) phenomena and enables the visualization of single biocells, bacteria, viruses, and biological tissues, providing monitoring of functional biosystems in vitro and in vivo, and the imaging-guided transportation of drug molecules. There is a variety of FL biolabels such as organic molecular dyes, genetically encoded fluorescent proteins (green fluorescent protein and homologs), semiconductor quantum dots, carbon dots, plasmonic metal gold-based nanostructures and more. In this review, a new generation of FL biolabels based on the recently found biophotonic effects of visible FL are described. This intrinsic FL phenomenon is observed in any peptide/protein materials folded into β-sheet secondary structures, irrespective of their composition, complexity, and origin. The FL effect has been observed both in natural amyloid fibrils, associated with neurodegenerative diseases (Alzheimer’s, Parkinson’s, and more), and diverse synthetic peptide/protein structures subjected to thermally induced biological refolding helix-like→β-sheet. This approach allowed us to develop a new generation of FL peptide/protein bionanodots radiating multicolor, tunable, visible FL, covering the entire visible spectrum in the range of 400–700 nm. Newly developed biocompatible nanoscale biomarkers are considered as a promising tool for emerging precise biomedicine and advanced medical nanotechnologies (high-resolution bioimaging, light diagnostics, therapy, optogenetics, and health monitoring). Full article
(This article belongs to the Special Issue Structure and Properties of Organic Dyes in Solid State)
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