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Advanced Functional Dyes
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Advanced Functional Dyes

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

Deadline for manuscript submissions: closed (15 January 2018) | Viewed by 39244

Special Issue Editor

Prof. Dr. Chen-Yu Yeh

E-Mail Website
Guest Editor
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan
Interests: dye-sensitized solar cells; electrochemistry; hole-transporting materials; porphyrins; organic dyes; organic solar cells
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

For thousands of years, organic dyes and pigments from natural materials, such as leaves, roots, bark, nuts, and flowers, have been used for coloration of silk, cotton, and wood by means of dyeing techniques. The first synthetic dye was discovered by British chemist William H. Perkin in 1856. Since then, thousands of organic dyes have been synthetized and widely used on a large scale for fibres, plastics, inks, paints, and liquids. In addition to traditional applications, organic dyes have attracted increasing attention for their high-technology applications in dye solar cells, photochromic materials, organic light emitting devices, organic semiconductor, hole-transporting materials, biological imaging, sensors, and photodynamic therapy. These dyes, the molecular structures of which are specifically designed, are named functional dyes.

In this respect, researchers working in this area are cordially invited to submit their manuscripts relevant to the synthesis, fundamental studies, or applications of functional dyes.

Prof. Dr. Chen-Yu Yeh
Guest Editor

Manuscript Submission Information

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Keywords

  • Biological imaging
  • Electronic materials
  • Optical materials
  • Optoelectronics
  • Photochromic materials

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Published Papers (7 papers)

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Research

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10 pages, 1872 KiB  
Article
Quantum Chemical Design Guidelines for Absorption and Emission Color Tuning of fac-Ir(ppy)3 Complexes
by Yoshiki Natori, Yasutaka Kitagawa, Shogo Aoki, Rena Teramoto, Hayato Tada, Iori Era and Masayoshi Nakano
Molecules 2018, 23(3), 577; https://doi.org/10.3390/molecules23030577 - 5 Mar 2018
Cited by 7 | Viewed by 5917
Abstract
The fac-Ir(ppy)3 complex, where ppy denotes 2-phenylpyridine, is one of the well-known luminescent metal complexes having a high quantum yield. However, there have been no specific molecular design guidelines for color tuning. For example, it is still unclear how its optical [...] Read more.
The fac-Ir(ppy)3 complex, where ppy denotes 2-phenylpyridine, is one of the well-known luminescent metal complexes having a high quantum yield. However, there have been no specific molecular design guidelines for color tuning. For example, it is still unclear how its optical properties are changed when changing substitution groups of ligands. Therefore, in this study, differences in the electronic structures and optical properties among several substituted fac-Ir(ppy)3 derivatives are examined in detail by density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations. On the basis of those results, we present rational design guidelines for absorption and emission color tuning by modifying the species of substituents and their substitution positions. Full article
(This article belongs to the Special Issue Advanced Functional Dyes)
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8 pages, 1465 KiB  
Article
Electronic Structure of C60/Zinc Phthalocyanine/V2O5 Interfaces Studied Using Photoemission Spectroscopy for Organic Photovoltaic Applications
by Chang Jin Lim, Min Gyu Park, Min Su Kim, Jeong Hwa Han, Soohaeng Cho, Mann-Ho Cho, Yeonjin Yi, Hyunbok Lee and Sang Wan Cho
Molecules 2018, 23(2), 449; https://doi.org/10.3390/molecules23020449 - 18 Feb 2018
Cited by 14 | Viewed by 5365
Abstract
The interfacial electronic structures of a bilayer of fullerene (C60) and zinc phthalocyanine (ZnPc) grown on vanadium pentoxide (V2O5) thin films deposited using radio frequency sputtering under various conditions were studied using X-ray and ultraviolet photoelectron spectroscopy. [...] Read more.
The interfacial electronic structures of a bilayer of fullerene (C60) and zinc phthalocyanine (ZnPc) grown on vanadium pentoxide (V2O5) thin films deposited using radio frequency sputtering under various conditions were studied using X-ray and ultraviolet photoelectron spectroscopy. The energy difference between the highest occupied molecular orbital (HOMO) level of the ZnPc layer and the lowest unoccupied molecular orbital (LUMO) level of the C60 layer was determined and compared with that grown on an indium tin oxide (ITO) substrate. The energy difference of a heterojunction on all V2O5 was found to be 1.3~1.4 eV, while that on ITO was 1.1 eV. This difference could be due to the higher binding energy of the HOMO of ZnPc on V2O5 than that on ITO regardless of work functions of the substrates. We also determined the complete energy level diagrams of C60/ZnPc on V2O5 and ITO. Full article
(This article belongs to the Special Issue Advanced Functional Dyes)
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20 pages, 4213 KiB  
Article
Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study
by Joshua J. Sutton, Jonathan E. Barnsley, Joseph I. Mapley, Pawel Wagner, David L. Officer and Keith C. Gordon
Molecules 2018, 23(2), 421; https://doi.org/10.3390/molecules23020421 - 14 Feb 2018
Cited by 10 | Viewed by 5149
Abstract
A series of eight carbazole-cyanoacrylate based donor-acceptor dyes were studied. Within the series the influence of modifying the thiophene bridge, linking donor and acceptor and a change in the nature of the acceptor, from acid to ester, was explored. In this joint experimental [...] Read more.
A series of eight carbazole-cyanoacrylate based donor-acceptor dyes were studied. Within the series the influence of modifying the thiophene bridge, linking donor and acceptor and a change in the nature of the acceptor, from acid to ester, was explored. In this joint experimental and computational study we have used electronic absorbance and emission spectroscopies, Raman spectroscopy and computational modeling (density functional theory). From these studies it was found that extending the bridge length allowed the lowest energy transition to be systematically red shifted by 0.12 eV, allowing for limited tuning of the absorption of dyes using this structural motif. Using the aforementioned techniques we demonstrate that this transition is charge transfer in nature. Furthermore, the extent of charge transfer between donor and acceptor decreases with increasing bridge length and the bridge plays a smaller role in electronically mixing with the acceptor as it is extended. Full article
(This article belongs to the Special Issue Advanced Functional Dyes)
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11 pages, 2645 KiB  
Article
Development of Functional Phthalocyanine-Based Associate towards an Effective Fluorimetric Detection of Hg(II)
by Guang-Xin Du, Tao Zhou, Meng-Lin Guo, Ping Huang, Ya-Bin Deng and Dong-Hui Li
Molecules 2018, 23(2), 418; https://doi.org/10.3390/molecules23020418 - 14 Feb 2018
Cited by 2 | Viewed by 3662
Abstract
In acidic media, cationic phthalocyanine Alcian blue 8GX, has an efficient fluorescence quenching effect on anionic phthalocyanine tetrasulphoaluminium phthalocyanines (AlS4Pc), forming an almost non-fluorescent associate. Based on this discovery, a red-emitting fluorescent probe consisted of AlS4PC and Alcian [...] Read more.
In acidic media, cationic phthalocyanine Alcian blue 8GX, has an efficient fluorescence quenching effect on anionic phthalocyanine tetrasulphoaluminium phthalocyanines (AlS4Pc), forming an almost non-fluorescent associate. Based on this discovery, a red-emitting fluorescent probe consisted of AlS4PC and Alcian blue 8GX has been developed through molecular assembly. Further studies indicated that the presence of Hg(II) ion has a significant fluorescence recovery effect of the probe. Notably, only Hg(II) can significantly restore the fluorescence of AlS4Pc-Alcian blue 8GX system which was revealed from the screening experiments of common metal ions, which confirmed that the fluorescence recovery by other metal ions is very weak or even unrestored, showing high specificity and sensitivity AlS4Pc-Alcian blue 8GX to Hg(II). Thus, a new fluorimetry for Hg(II) with high specificity and high sensitivity in a wide concentration range has been established using AlS4Pc-Alcian blue 8GX associate as a red-emitting fluorescent probe. It is more noteworthy that this study opens a new way for development and application of functional phthalocyanine based red-emitting fluorescent probes. Full article
(This article belongs to the Special Issue Advanced Functional Dyes)
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30 pages, 8201 KiB  
Article
Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media
by Rui Liu, Mengran Liu, Don Hood, Chih-Yuan Chen, Christopher J. MacNevin, Dewey Holten and Jonathan S. Lindsey
Molecules 2018, 23(1), 130; https://doi.org/10.3390/molecules23010130 - 10 Jan 2018
Cited by 13 | Viewed by 5729
Abstract
Fluorophores that absorb and emit in the red spectral region (600–700 nm) are of great interest in photochemistry and photomedicine. Eight new target chlorins (and 19 new chlorins altogether)—analogues of chlorophyll—of different polarities have been designed and synthesized for various applications; seven of [...] Read more.
Fluorophores that absorb and emit in the red spectral region (600–700 nm) are of great interest in photochemistry and photomedicine. Eight new target chlorins (and 19 new chlorins altogether)—analogues of chlorophyll—of different polarities have been designed and synthesized for various applications; seven of the chlorins are equipped with a bioconjugatable tether. Hydrophobic or amphiphilic chlorins in a non-polar organic solvent (toluene), polar organic solvent (DMF), and aqueous or aqueous micellar media show a sharp emission band in the red region and modest fluorescence quantum yield (Φf = 0.2–0.3). A Poisson analysis implies most micelles are empty and few contain >1 chlorin. Water-soluble chlorins each bearing three PEG (oligoethyleneglycol) groups exhibit narrow emission bands (full-width-at-half maximum <25 nm). The lifetime of the lowest singlet excited state and the corresponding yields and rate constants for depopulation pathways (fluorescence, intersystem crossing, internal conversion) are generally little affected by the PEG groups or dissolution in aqueous or organic media. A set of chlorin–avidin conjugates revealed a 2-fold increase in Φf with increased average chlorin/avidin ratio (2.3–12). In summary, the chlorins of various polarities described herein are well suited as red-emitting fluorophores for applications in aqueous or organic media. Full article
(This article belongs to the Special Issue Advanced Functional Dyes)
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11 pages, 609 KiB  
Article
Synthesis of Novel Reactive Disperse Silicon-Containing Dyes and Their Coloring Properties on Silicone Rubbers
by Ning Yu, Shufen Zhang, Bingtao Tang, Wei Ma and Jinjing Qiu
Molecules 2018, 23(1), 127; https://doi.org/10.3390/molecules23010127 - 9 Jan 2018
Cited by 7 | Viewed by 4898
Abstract
Novel red and purple reactive disperse silicon-containing dyes were designed and synthesized using p-nitroaniline and 6-bromo-2,4-dinitro-aniline as diazonium components, the first condensation product of cyanuric chloride and 3-(N,N-diethyl)amino-aniline as coupling component, and 3-aminopropylmethoxydimethylsilane, 3-aminopropylmethyldimethoxysilane, and 3-aminopropyltrimethoxysilane as silicone [...] Read more.
Novel red and purple reactive disperse silicon-containing dyes were designed and synthesized using p-nitroaniline and 6-bromo-2,4-dinitro-aniline as diazonium components, the first condensation product of cyanuric chloride and 3-(N,N-diethyl)amino-aniline as coupling component, and 3-aminopropylmethoxydimethylsilane, 3-aminopropylmethyldimethoxysilane, and 3-aminopropyltrimethoxysilane as silicone reactive agents. These dyes were characterized by UV-Vis, 1H-NMR, FT-IR, and MS. The obtained reactive disperse silicon-containing dyes were used to color silicone rubbers and the color fastness of the dyes were evaluated. The dry/wet rubbing and washing fastnesses of these dyes all reached 4–5 grade and the sublimation fastness was also above 4 grade, indicating outstanding performance in terms of color fastness. Such colored silicone rubbers showed bright and rich colors without affecting its static mechanical properties. Full article
(This article belongs to the Special Issue Advanced Functional Dyes)
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Review

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34 pages, 63431 KiB  
Review
Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group
by Mário M. Q. Simões, Daniel T. G. Gonzaga, Mariana F. C. Cardoso, Luana Da S. M. Forezi, Ana T. P. C. Gomes, Fernando De C. Da Silva, Vítor F. Ferreira, Maria G. P. M. S. Neves and José A. S. Cavaleiro
Molecules 2018, 23(4), 792; https://doi.org/10.3390/molecules23040792 - 29 Mar 2018
Cited by 22 | Viewed by 7754
Abstract
Carbene transfer reactions are very important transformations in organic synthesis, allowing the generation of structurally challenging products by catalysed cyclopropanation, cyclopropenation, carbene C-H, N-H, O-H, S-H, and Si-H insertion, and olefination of carbonyl compounds. In particular, chiral and achiral metalloporphyrins have been successfully [...] Read more.
Carbene transfer reactions are very important transformations in organic synthesis, allowing the generation of structurally challenging products by catalysed cyclopropanation, cyclopropenation, carbene C-H, N-H, O-H, S-H, and Si-H insertion, and olefination of carbonyl compounds. In particular, chiral and achiral metalloporphyrins have been successfully explored as biomimetic catalysts for these carbene transfer reactions under both homogeneous and heterogeneous conditions. In this work the use of synthetic metalloporphyrins (MPorph, M = Fe, Ru, Os, Co, Rh, Ir, Sn) as homogeneous or heterogeneous catalysts for carbene transfer reactions in the last years is reviewed, almost exclusively focused on the literature since the year 2010, except when reference to older publications was deemed to be crucial. Full article
(This article belongs to the Special Issue Advanced Functional Dyes)
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