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Advances in Functional Organic Dye Chemistry
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Advances in Functional Organic Dye Chemistry

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

Deadline for manuscript submissions: closed (31 December 2024) | Viewed by 10214

Special Issue Editor

Dr. Agostina-Lina Capodilupo

E-Mail Website
Guest Editor
Italian National Research Council | CNR, Institute of Nanotechnology, Rome, Italy
Interests: organic dyes; organic emissive materials; organic semiconductors; open-shell organic conjugated materials; electrochromic organic materials; electrofluorochromic organic materials; self-assembly into organic materials
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Functional organic dyes are materials designed and synthesized with specific physicochemical properties to be key elements in several technological fields. These materials play a crucial role in various optoelectronic fields as well as in medical and biological research. Proof of the importance of functional organic dyes are the significant progresses in the fields  of light-emitting diodes (OLED), organic photovoltaics (OPV), electrochromic devices (ECD) and electrochromic devices (EFC), fluorescent probes for biodiagnostics, photodynamic therapy (PDT), and photonic organic crystals. Molecular design and organic synthesis represent a fundamental tool for the development of new functional organic dyes. This Special Issue entitled “Advances in Functional Organic Dye Chemistry” welcomes manuscripts (original research papers, short communications, or focus reviews) presenting results from current studies performed predominantly in the research areas pointed out by the keywords given below. However, other related topics are also welcome.

Dr. Agostina-Lina Capodilupo
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. Molecules is an international peer-reviewed open access semimonthly 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 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

  • organic dyes
  • organic semiconductors
  • photonic organic crystals
  • organic emissive materials
  • organic electrochromic materials
  • organic electrofluorochromic materials
  • molecular sensors

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Published Papers (7 papers)

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Research

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14 pages, 5415 KiB  
Article
Amphiphilic Styrene-Based Pyrene Derivatives: Tunable Aggregation Luminescence and Their Photo-Induced Dimerization Behavior
by Junying Zhang, Xingwei Luo and Juan Qiu
Molecules 2025, 30(8), 1719; https://doi.org/10.3390/molecules30081719 - 11 Apr 2025
Viewed by 241
Abstract
Since the discovery of the aggregation-induced emission (AIE) phenomenon, various stimuli-responsive materials have been rapidly developed. However, how to achieve the transition between aggregation-caused quenching (ACQ) and AIE through molecular design is an urgent problem to be solved. In this work, we synthesized [...] Read more.
Since the discovery of the aggregation-induced emission (AIE) phenomenon, various stimuli-responsive materials have been rapidly developed. However, how to achieve the transition between aggregation-caused quenching (ACQ) and AIE through molecular design is an urgent problem to be solved. In this work, we synthesized and studied the aggregation luminescence behavior and photochromism of two different substituted pyrene ethylene derivatives, 1-H and 1-CN. Due to the different substituents attached to the ethylene unit, 1-H exhibits ACQ luminescence behavior. When the substituent is a cyanide group, it exhibits AIE behavior. In addition, the ordered nanoparticles formed by self-assembly in aqueous solution exhibit interesting photo-induced cyclization behavior, which leads to fluorescence quenching under ultraviolet light irradiation (λ = 365 nm). Therefore, due to their amphiphilicity and photo-responsiveness, these compounds can be used as anticounterfeiting inks in information encryption. This work contributes new members to the family of amphiphilic photo-responsive materials and demonstrates their potential applications in optical information storage and multi-color luminescence. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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14 pages, 3394 KiB  
Article
Asymmetric Donor–Acceptor 2,7-Disubstituted Fluorenes and Their 9-Diazoderivatives: Synthesis, Optical Spectra and Photolysis
by Andrei I. Savchenko, Vladimir N. Belov, Mariano L. Bossi and Stefan W. Hell
Molecules 2025, 30(2), 321; https://doi.org/10.3390/molecules30020321 - 15 Jan 2025
Viewed by 655
Abstract
In a search for dyes photoactivatable with visible light, fluorenes with substituents at positions 2 and 7 were prepared, and their absorption and emission spectra were studied. In particular, the synthesis route to 9-diazofluorenes with 2-(N,N-dialkylamino) and N-modified 7-(4-pyridyl) substituents was established. These [...] Read more.
In a search for dyes photoactivatable with visible light, fluorenes with substituents at positions 2 and 7 were prepared, and their absorption and emission spectra were studied. In particular, the synthesis route to 9-diazofluorenes with 2-(N,N-dialkylamino) and N-modified 7-(4-pyridyl) substituents was established. These compounds are initially non-fluorescent, undergo photolysis with UV or blue light, and—in non-polar media—provide orange- to red-emitting products with a large separation between absorption and emission bands. Irradiation of non-fluorescent 9-diazoderivative 20 in dioxane with the light of 365 nm or 470 nm was accompanied by strong fluorescence gain (10 to 20 times), orange–red emission, and a large Stokes shift of photoproducts, which structurally relate to fluorescent betaine 13 (model compound without diazo group). Photolysis of 20 in protic solvents (ROH = MeOH, H2O) provided clean transformation to C9-OR derivatives, though the emission gain in protic solvents was low. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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15 pages, 2759 KiB  
Article
Multicomponent Synthesis of New Fluorescent Boron Complexes Derived from 3-Hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde
by Viktorija Savickienė, Aurimas Bieliauskas, Sergey Belyakov, Eglė Arbačiauskienė and Algirdas Šačkus
Molecules 2024, 29(14), 3432; https://doi.org/10.3390/molecules29143432 - 22 Jul 2024
Cited by 1 | Viewed by 1708
Abstract
Novel fluorescent pyrazole-containing boron (III) complexes were synthesized employing a one-pot three-component reaction of 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde, 2-aminobenzenecarboxylic acids, and boronic acids. The structures of the novel heterocyclic compounds were confirmed using 1H-, 13C-, 15N-, 19F-, and 11B-NMR, [...] Read more.
Novel fluorescent pyrazole-containing boron (III) complexes were synthesized employing a one-pot three-component reaction of 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde, 2-aminobenzenecarboxylic acids, and boronic acids. The structures of the novel heterocyclic compounds were confirmed using 1H-, 13C-, 15N-, 19F-, and 11B-NMR, IR spectroscopy, HRMS, and single-crystal X-ray diffraction data. The photophysical properties of the obtained iminoboronates were investigated using spectroscopic techniques, such as UV–vis and fluorescence spectroscopies. Compounds display main UV–vis absorption maxima in the blue region, and fluorescence emission maxima are observed in the green region of the visible spectrum. It was revealed that compounds exhibit fluorescence quantum yield up to 4.3% in different solvents and demonstrate an aggregation-induced emission enhancement effect in mixed THF–water solutions. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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14 pages, 3799 KiB  
Article
Preparation of Dye Semiconductors via Coupling Polymerization Catalyzed by Two Catalysts and Application to Transistor
by Shiwei Ren, Wenqing Zhang, Zhuoer Wang, Abderrahim Yassar, Jinyang Chen, Minfeng Zeng and Zhengran Yi
Molecules 2024, 29(1), 71; https://doi.org/10.3390/molecules29010071 - 22 Dec 2023
Cited by 3 | Viewed by 1512
Abstract
Organic dye semiconductors have received increasing attention as the next generation of semiconductors, and one of their potential applications is as a core component of organic transistors. In this study, two novel diketopyrrolopyrrole (DPP) dye core-based materials were designed and separately prepared using [...] Read more.
Organic dye semiconductors have received increasing attention as the next generation of semiconductors, and one of their potential applications is as a core component of organic transistors. In this study, two novel diketopyrrolopyrrole (DPP) dye core-based materials were designed and separately prepared using Stille coupling reactions under different palladium catalyst conditions. The molecular weights and elemental compositions were tested to demonstrate that both catalysts could be used to successfully prepare materials of this structure, with the main differences being the weight-average molecular weight and the dispersion index. PDPP-2Py-2Tz I with a longer conjugation length exhibited better thermodynamic stability than the counterpart polymer PDPP-2Py-2Tz II. The intrinsic optical properties of the polymers were relatively similar, while the electrochemical tests showed small differences in their energy levels. The polymers obtained with different catalysts displayed similar and moderate electron mobility in transistor devices, while PDPP-2Py-2Tz I possessed a higher switching ratio. Our study provides a comparison of such dye materials under different catalytic conditions and also demonstrates the great potential of dye materials for optoelectronic applications. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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17 pages, 3202 KiB  
Article
Rational Design of Cost-Effective 4-Styrylcoumarin Fluorescent Derivatives for Biomolecule Labeling
by Raquel Eustáquio, João P. Prates Ramalho, Ana Teresa Caldeira and António Pereira
Molecules 2023, 28(19), 6822; https://doi.org/10.3390/molecules28196822 - 27 Sep 2023
Cited by 3 | Viewed by 1284
Abstract
Fluorescent labels are key tools in a wide range of modern scientific applications, such as fluorescence microscopy, flow cytometry, histochemistry, direct and indirect immunochemistry, and fluorescence in situ hybridization (FISH). Small fluorescent labels have important practical advantages as they allow maximizing the fluorescence [...] Read more.
Fluorescent labels are key tools in a wide range of modern scientific applications, such as fluorescence microscopy, flow cytometry, histochemistry, direct and indirect immunochemistry, and fluorescence in situ hybridization (FISH). Small fluorescent labels have important practical advantages as they allow maximizing the fluorescence signal by binding multiple fluorophores to a single biomolecule. At present, the most widely used fluorescent labels available present small Stokes shifts and are too costly to be used in routine applications. In this work we present four new coumarin derivatives, as promising and inexpensive fluorescent labels for biomolecules, obtained through a cost-effective, efficient, and straightforward synthetic strategy. Density functional theory and time-dependent density functional theory calculations of the electronic ground and lowest-lying singlet excited states were carried out in order to gain insights into the observed photophysical properties. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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Review

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35 pages, 20847 KiB  
Review
The ATTO 565 Dye and Its Applications in Microscopy
by Yuheng Wu and René M. Williams
Molecules 2024, 29(17), 4243; https://doi.org/10.3390/molecules29174243 - 6 Sep 2024
Viewed by 1419
Abstract
ATTO 565, a Rhodamine-type dye, has garnered significant attention due to its remarkable optical properties, such as a high fluorescence quantum yield, and the fact that it is a relatively stable structure and has low biotoxicity. ATTO 565 has found extensive applications in [...] Read more.
ATTO 565, a Rhodamine-type dye, has garnered significant attention due to its remarkable optical properties, such as a high fluorescence quantum yield, and the fact that it is a relatively stable structure and has low biotoxicity. ATTO 565 has found extensive applications in combination with microscopy technology. In this review, the chemical and optical properties of ATTO 565 are introduced, along with the principles behind them. The functionality of ATTO 565 in confocal microscopy, stimulated emission depletion (STED) microscopy, single-molecule tracking (SMT) techniques, two-photon excitation–stimulated emission depletion microscopy (TPE-STED) and fluorescence correlation spectroscopy (FCS) is discussed. These studies demonstrate that ATTO 565 plays a crucial role in areas such as biological imaging and single-molecule localization, thus warranting further in-depth investigations. Finally, we present some prospects and concepts for the future applications of ATTO 565 in the fields of biocompatibility and metal ion detection. This review does not include theoretical calculations for the ATTO 565 molecule. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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20 pages, 8078 KiB  
Review
Advances in Organic Fluorescent Probes for Intracellular Zn2+ Detection and Bioimaging
by Yi Chen
Molecules 2024, 29(11), 2542; https://doi.org/10.3390/molecules29112542 - 28 May 2024
Cited by 7 | Viewed by 1815
Abstract
Zinc ions (Zn2+) play a key role in maintaining and regulating protein structures and functions. To better understand the intracellular Zn2+ homeostasis and signaling role, various fluorescent sensors have been developed that allow the monitoring of Zn2+ concentrations and [...] Read more.
Zinc ions (Zn2+) play a key role in maintaining and regulating protein structures and functions. To better understand the intracellular Zn2+ homeostasis and signaling role, various fluorescent sensors have been developed that allow the monitoring of Zn2+ concentrations and bioimaging in live cells in real time. This review highlights the recent development of organic fluorescent probes for the detection and imaging of intracellular Zn2+, including the design and construction of the probes, fluorescent response mechanisms, and their applications to intracellular Zn2+ detection and imaging on-site. Finally, the current challenges and prospects are discussed. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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