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Chemosensors
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Organic Fluorescent Materials as Chemical Sensors
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Organic Fluorescent Materials as Chemical Sensors

A special issue of Chemosensors (ISSN 2227-9040). This special issue belongs to the section "Optical Chemical Sensors".

Deadline for manuscript submissions: closed (15 September 2021) | Viewed by 36984

Special Issue Editor

Dr. Yinyin Bao

E-Mail Website
Guest Editor
Institute of Pharmaceutical Sciences, Department of Chemistry and Applied Sciences, ETH Zurich, 8093 Zurich, Switzerland
Interests: fluorescent chemosensors; nanosensors; bioimaging; drug delivery; nanomedicine; fluorescent polymers; biodegradable polymers; 3D printing; medical devices
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Since the Nobel Prize in Chemistry was awarded to Roger Y. Tsien, Osamu Shimomura, and Martin Chalfie in 2008 due to the discovery and applications of Green Fluorescent Protein, a number of fluorescent organic molecules, synthetic polymers, and the assembled nanomaterials have been developed as chemical sensors, exhibiting great potential in various applications, such as bioimaging, disease diagnostics, environmental analysis, etc. In particular, the fluorescence sensing strategy can provide many advantages, including high sensitivity and selectivity, in situ detection, rapid response, simple set-up, and low cost, compared to conventional analytical techniques. Through the investigation of structure–property relationships as well as nanoformulation, the performance of these chemical sensors can be further optimized.

In the early stage of the development of fluorescent sensors, photoinduced electron transfer (PET), intramolecular charge transfer (ICT), Förster resonance energy transfer (FRET), and excited state intramolecular proton transfer (ESIPT) were extensively applied to the design and synthesis of highly efficient chemical probes and imaging agents. In recent years, aggregation-induced emission (AIE), thermally activated delayed fluorescence (TADF), and room-temperature phosphorescence (RTP) have emerged as hot topics in the field of light-emitting materials. In combination with different platforms such as organic molecules, conjugated/non-conjugated polymers, organic/polymeric nanoassemblies, and organic–inorganic hybrid nanomaterials, fluorescent chemosensors have entered an age of unprecedented prosperity, benefiting from the various sensing mechanisms available.

In this Special Issue, we will publish a collection of manuscripts that describe the latest advances on chemical sensors based on organic/polymeric fluorescent materials. New molecules, polymers, nanomaterials, sensing strategies, and applications will be reported, and focus will be given to the structure–property investigations. Topics of interest include but are not limited to:

  • Organic fluorophores;
  • Fluorescent and phosphorescent polymers;
  • Emissive nanomaterials;
  • Aggregation-induced emissive materials;
  • Stimulus-responsive materials;
  • Chemical sensing;
  • Bioimaging;
  • Environmental analysis;
  • Image-guided drug delivery;
  • Phototherapy and theranostics.

Dr. Yinyin Bao
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. Chemosensors 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 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.

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Published Papers (9 papers)

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Editorial

Jump to: Research, Review

2 pages, 182 KiB  
Editorial
Editorial: Organic Fluorescent Materials as Chemical Sensors
by Yinyin Bao
Chemosensors 2021, 9(11), 308; https://doi.org/10.3390/chemosensors9110308 - 28 Oct 2021
Cited by 3 | Viewed by 1885
Abstract
The last two decades have witnessed a significant development of fluorescent chemosensors with high sensitivity and selectivity, fast response and in situ detection [...] Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)

Research

Jump to: Editorial, Review

17 pages, 1756 KiB  
Article
A Novel Dialkylamino GFP Chromophore as an Environment-Polarity Sensor Reveals the Role of Twisted Intramolecular Charge Transfer
by Cheng Chen, Sean A. Boulanger, Anatolii I. Sokolov, Mikhail S. Baranov and Chong Fang
Chemosensors 2021, 9(8), 234; https://doi.org/10.3390/chemosensors9080234 - 23 Aug 2021
Cited by 14 | Viewed by 3943
Abstract
We discovered a novel fluorophore by incorporating a dimethylamino group (–NMe2) into the conformationally locked green fluorescent protein (GFP) scaffold. It exhibited a marked solvent-polarity-dependent fluorogenic behavior and can potentially find broad applications as an environment-polarity sensor in vitro and in [...] Read more.
We discovered a novel fluorophore by incorporating a dimethylamino group (–NMe2) into the conformationally locked green fluorescent protein (GFP) scaffold. It exhibited a marked solvent-polarity-dependent fluorogenic behavior and can potentially find broad applications as an environment-polarity sensor in vitro and in vivo. The ultrafast femtosecond transient absorption (fs-TA) spectroscopy in combination with quantum calculations revealed the presence of a twisted intramolecular charge transfer (TICT) state, which is formed by rotation of the –NMe2 group in the electronic excited state. In contrast to the bright fluorescent state (FS), the TICT state is dark and effectively quenches fluorescence upon formation. We employed a newly developed multivariable analysis approach to the FS lifetime in various solvents and showed that the FS → TICT reaction barrier is mainly modulated by H-bonding capability instead of viscosity of the solvent, accounting for the observed polarity dependence. These deep mechanistic insights are further corroborated by the dramatic loss of fluorogenicity for two similar GFP-derived chromophores in which the rotation of the –NMe2 group is inhibited by structural locking. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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18 pages, 5116 KiB  
Article
BODIPY-Pyridylhydrazone Probe for Fluorescence Turn-On Detection of Fe3+ and Its Bioimaging Application
by Jukkrit Nootem, Chanchai Sattayanon, Rathawat Daengngern, Anyanee Kamkaew, Worawat Wattanathana, Suttipong Wannapaiboon, Paitoon Rashatasakhon and Kantapat Chansaenpak
Chemosensors 2021, 9(7), 165; https://doi.org/10.3390/chemosensors9070165 - 2 Jul 2021
Cited by 17 | Viewed by 3922
Abstract
A novel pyridylhydrazone-tethered BODIPY (BODIPY-PH) was synthesized, fully characterized via nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopic (FTIR), and single-crystal X-ray diffraction (SC-XRD) techniques, and developed for the selective detection of Fe3+ through fluorescent enhancement process. This derivative showed 1:1 binding [...] Read more.
A novel pyridylhydrazone-tethered BODIPY (BODIPY-PH) was synthesized, fully characterized via nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopic (FTIR), and single-crystal X-ray diffraction (SC-XRD) techniques, and developed for the selective detection of Fe3+ through fluorescent enhancement process. This derivative showed 1:1 binding with Fe3+ in an acetonitrile-water mixture (1:9 v/v) with the binding constant (K) of 5.4 × 104 M−1 and the limit of detection of 0.58 µM. The Fe3+ complexation reaction has been proved to be a reversible process and could be effectively repeated up to three cycles. The electronic properties of BODIPY-PH and its Fe3+ complex modeled by the density functional theory (DFT) method suggested the presence of chelation-enhanced fluorescence (CHEF) effect in the Fe3+ binding reaction. The X-ray absorption spectroscopy (XAS) probed at Fe K-edge confirmed the complex formation between BODIPY-PH and the Fe3+ in an octahedral geometry. Finally, bioimaging against human embryonic kidney (Hek293) cell, through confocal fluorescence microscopic technique indicated that the BODIPY-PH displayed good permeability and low toxicity toward the tested cell lines and showed enhanced fluorescent signal in the cells incubated with Fe3+ proving its capability for Fe3+ analysis in cellular matrix. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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11 pages, 2774 KiB  
Article
Molecular Rotors with Aggregation-Induced Emission (AIE) as Fluorescent Probes for the Control of Polyurethane Synthesis
by Pierpaolo Minei, Giuseppe Iasilli, Giacomo Ruggeri, Virgilio Mattoli and Andrea Pucci
Chemosensors 2021, 9(1), 3; https://doi.org/10.3390/chemosensors9010003 - 23 Dec 2020
Cited by 8 | Viewed by 3908
Abstract
In this work, the use of fluorescent molecular rotors such as 9-(2,2-dicyanovinyl)julolidine (DCVJ) and 2,3-bis(4-(phenyl(4-(1,2,2-triphenylvinyl) phenyl)amino)phenyl)fumaronitrile (TPETPAFN) was proposed for the real-time monitoring of polyurethane (PU) formation in a solution of dimethylacetamide starting with 4,4′-methylenediphenyl diisocyanate (MDI) and different polyethylene glycols (PEG400 and [...] Read more.
In this work, the use of fluorescent molecular rotors such as 9-(2,2-dicyanovinyl)julolidine (DCVJ) and 2,3-bis(4-(phenyl(4-(1,2,2-triphenylvinyl) phenyl)amino)phenyl)fumaronitrile (TPETPAFN) was proposed for the real-time monitoring of polyurethane (PU) formation in a solution of dimethylacetamide starting with 4,4′-methylenediphenyl diisocyanate (MDI) and different polyethylene glycols (PEG400 and PEG600) as diols. Notably, relative viscosity variations were compared with fluorescence changes, recorded as a function of the polymerization progress. The agreement between these two parameters suggested the innovative use of a low-cost fluorescence detection system based on a LED/photodiode assembly directly mountable on the reaction apparatus. The general validity of the proposed experiments enabled the monitoring of polyurethane polymerization and suggested its effective applications to a variety of industrial polymers, showing viscosity enhancement during polymerization. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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12 pages, 3123 KiB  
Article
A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite
by Yasuhiro Shiraishi, Rikako Nakatani, Shunsuke Takagi, Chiharu Yamada and Takayuki Hirai
Chemosensors 2020, 8(4), 123; https://doi.org/10.3390/chemosensors8040123 - 1 Dec 2020
Cited by 15 | Viewed by 3738
Abstract
Hypochlorite anion (ClO−) is a widely-used disinfectant and a microbicidal agent in the immune system. Accurate detection of ClO− in environmental and biological samples by simply prepared chemosensors/chemodosimeters is important. Herein, we report that a naphthalimide–sulfonylhydrazine conjugate with an imine [...] Read more.
Hypochlorite anion (ClO−) is a widely-used disinfectant and a microbicidal agent in the immune system. Accurate detection of ClO− in environmental and biological samples by simply prepared chemosensors/chemodosimeters is important. Herein, we report that a naphthalimide–sulfonylhydrazine conjugate with an imine (C=N) linker, prepared via simple condensation, acts as an effective fluorescent chemodosimeter for ClO−. The molecule exhibits a weak emission, but ClO−-selective cleavage of its C=N bond creates a strong green emission. Ab initio calculation showed that the emission enhancement by ClO− originates from the suppression of intramolecular electron transfer from the photoexcited naphthalimide through the C=N linker. This response enables selective and sensitive detection of ClO− at physiological pH range (7–9) and allows fluorometric ClO− imaging in the presence of cells. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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Review

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32 pages, 6799 KiB  
Review
Squaraine-Based Optical Sensors: Designer Toolbox for Exploring Ionic and Molecular Recognitions
by Daniel D. Ta and Sergei V. Dzyuba
Chemosensors 2021, 9(11), 302; https://doi.org/10.3390/chemosensors9110302 - 25 Oct 2021
Cited by 13 | Viewed by 3769
Abstract
Small molecule-based chromogenic and fluorogenic probes play an indispensable role in many sensing applications. Ideal optical chemosensors should provide selectivity and sensitivity towards a variety of analytes. Synthetic accessibility and attractive photophysical properties have made squaraine dyes an enticing platform for the development [...] Read more.
Small molecule-based chromogenic and fluorogenic probes play an indispensable role in many sensing applications. Ideal optical chemosensors should provide selectivity and sensitivity towards a variety of analytes. Synthetic accessibility and attractive photophysical properties have made squaraine dyes an enticing platform for the development of chemosensors. This review highlights the versatility of modular assemblies of squaraine-based chemosensors and chemodosimeters that take advantage of the availability of various structurally and functionally diverse recognition motifs, as well as utilizing additional recognition capabilities due to the unique structural features of the squaraine ring. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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15 pages, 22826 KiB  
Review
Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes
by Yingchun Wang, Tomas Opsomer and Wim Dehaen
Chemosensors 2021, 9(1), 16; https://doi.org/10.3390/chemosensors9010016 - 15 Jan 2021
Cited by 8 | Viewed by 3584
Abstract
The 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies involving click−cyclization−aromatization domino reactions, [...] Read more.
The 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies involving click−cyclization−aromatization domino reactions, gold-catalyzed cyclization of propargyl triazoles or triazolization of acetophenones. As a result, TAPs with diverse substitution patterns were obtained, showing varying fluorescence properties. Based on these properties, several TAPs have been selected and studied as fluorescent imaging probes in living cells and as sensors. This mini review provides an overview of the research on the bicyclic TAPs and does not comment on the literature about benzo or otherwise fused systems. The synthetic methodologies for the preparation of TAPs, the substituent effects on the fluorescence properties, and the behavior of the TAP core as an element of biological imaging probes and sensors are discussed. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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26 pages, 18378 KiB  
Review
Perylene Imide-Based Optical Chemosensors for Vapor Detection
by Miao Zhang, Jiangfan Shi, Chenglong Liao, Qingyun Tian, Chuanyi Wang, Shuai Chen and Ling Zang
Chemosensors 2021, 9(1), 1; https://doi.org/10.3390/chemosensors9010001 - 22 Dec 2020
Cited by 16 | Viewed by 4222
Abstract
Perylene imide (PI) molecules and materials have been extensively studied for optical chemical sensors, particularly those based on fluorescence and colorimetric mode, taking advantage of the unique features of PIs such as structure tunability, good thermal, optical and chemical stability, strong electron affinity, [...] Read more.
Perylene imide (PI) molecules and materials have been extensively studied for optical chemical sensors, particularly those based on fluorescence and colorimetric mode, taking advantage of the unique features of PIs such as structure tunability, good thermal, optical and chemical stability, strong electron affinity, strong visible light absorption and high fluorescence quantum yield. PI-based optical chemosensors have now found broad applications in gas phase detection of chemicals, including explosives, biomarkers of some food and diseases (such as organic amines (alkylamines and aromatic amines)), benzene homologs, organic peroxides, phenols and nitroaromatics, etc. In this review, the recent research on PI-based fluorometric and colorimetric sensors, as well as array technology incorporating multiple sensors, is reviewed along with the discussion of potential applications in environment, health and public safety areas. Specifically, we discuss the molecular design and aggregate architecture of PIs in correlation with the corresponding sensor performances (including sensitivity, selectivity, response time, recovery time, reversibility, etc.). We also provide a perspective summary highlighting the great potential for future development of PIs optical chemosensors, especially in the sensor array format that will largely enhance the detection specificity in complexed environments. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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23 pages, 9902 KiB  
Review
Macrocyclic Arenes Functionalized with BODIPY: Rising Stars among Chemosensors and Smart Materials
by Jianjun Huang, Yuyu Fang and Wim Dehaen
Chemosensors 2020, 8(3), 51; https://doi.org/10.3390/chemosensors8030051 - 6 Jul 2020
Cited by 17 | Viewed by 6253
Abstract
Macrocycles play a crucial role in supramolecular chemistry and the family of macrocyclic arenes represents one of the most important types of hosts. Among them, calixarenes, resorcinarenes and pillararenes are the most commonly encountered macrocyclic arenes, and they have received considerable attention. Boron-dipyrromethene [...] Read more.
Macrocycles play a crucial role in supramolecular chemistry and the family of macrocyclic arenes represents one of the most important types of hosts. Among them, calixarenes, resorcinarenes and pillararenes are the most commonly encountered macrocyclic arenes, and they have received considerable attention. Boron-dipyrromethene (BODIPY) dyes are fascinating compounds with multiple functionalization sites and outstanding luminescence properties including high fluorescence quantum yields, large molar absorption coefficients and remarkable photo- and chemical stability. The combination of macrocyclic arenes and BODIPY dyes has been demonstrated to be an effective strategy to construct chemosensors for various guests and smart materials with tailored properties. Herein, we firstly summarize the recent advances made so far in macrocyclic arenes substituted with BODIPY. This review only focuses on the three macrocyclic arenes of calixarenes, resorcinarenes and pillararenes, as there are no other macrocyclic arenes substituted BODIPY units at the present time. Hopefully, this review will not only afford a guide and useful information for those who are interested in developing novel chemosensors and smart materials, but also inspire new opportunities in this field. Full article
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
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