4.7 Article Proceedings Paper

2,1,3-Benzothiadiazole-based fluorophores. Synthesis, electrochemical, thermal and photophysical characterization

期刊

DYES AND PIGMENTS
卷 135, 期 -, 页码 26-35

出版社

ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2016.07.011

关键词

2,1,3-Benzothiadiazole; Quadrupolar compounds; Photophysics; Fluorescence; Solvatochromism

向作者/读者索取更多资源

Three photoactive compounds with pi-extended conjugation based on the 2,1,3-benzothiadiazole unit were synthesized and characterized. The compounds exhibited absorption in the violet-blue region with molar absorptivity coefficients and radiative rate constants arising from spin and symmetry allowed (1)pi pi* electronic transitions. An emission located in the green region with a large Stokes shift was observed, which was most likely due to a charge-transfer mechanism in the excited state. In spin-coated films a dependence on the fluorescence emission intensity with the size of the alkoxy chain could be observed, where an effective non-radiactive channel seems to be present to deactivate the excited state. The thermal properties were analyzed by differential scanning calorimetry (DSC), and all final compounds exhibited a similar behavior with a crystal-isotropic liquid transition during the heating scan and isotropic liquid-crystal transition during the cooling process. Thermogravimetric analysis indicated a main thermal event with an initial decomposition temperature that was higher than 340 degrees C. The electrochemical characterization indicate that the compounds exhibited a reversible peak at -1.48 V and an irreversible oxidation process at 0.94 V versus Ag/Ag+. The electrochemical band gap was calculated to be approximately 2.30 eV versus NHE. The spectroelectrochemical measurements demonstrated changes in the absorption spectra due to changes in the electronic structure of the conjugated molecules under oxidative and reductive potentials. (C) 2016 Elsevier Ltd. All rights reserved.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Chemistry, Applied

Influence of different photoinitiatiors in the UV-LED curing of polyester acrylated varnishes

Ricardo Dossin, Alessandra Lavoratti, Rodrigo Cercena, Alexandre Goncalves Dal-bo, Matheus Vinicius Gregory Zimmermann, Ademir Jose Zattera

Summary: The search for environmentally friendly coatings, especially in the field of ultraviolet light curing, has become increasingly important in recent years. In this study, the influence of six types of photoinitiators on the curing of polyester acrylate varnishes was investigated. The results showed that all varnishes were completely cured, and the resins cured with LED 1711 and diphenyl (acyl) phosphine oxide exhibited the lowest post-curing photoyellowing.

JOURNAL OF COATINGS TECHNOLOGY AND RESEARCH (2023)

Article Chemistry, Physical

Suzuki Coupling in Troger's Bases: Overcoming Challenging Substrates through Aqueous Micellar Catalysis

Eduam O. Boeira, Caroline B. Pla, Fabiano S. Rodembusch, Angelica Moro

Summary: In this study, the arylation of Troger's base was achieved through the Suzuki cross-coupling reaction using aqueous micellar catalysis. The developed reaction conditions allowed for the preparation of various Troger's base derivatives with low catalytic loading of Pd(OAc)(2) catalyst and under environmentally friendly aqueous conditions.

CHEMCATCHEM (2023)

Article Chemistry, Applied

Mono-silylated 2,1,3-benzothiadiazole-based precursors. Molecular scaffolds for obtaining fluorescent organic-inorganic hybrid materials with tailored photophysical properties

Victoria G. Isoppo, Fabiano S. Rodembusch, Angelica V. Moro

Summary: The present study describes the synthesis of mono-silylated benzothiadiazole compounds and their use in obtaining organic-inorganic fluorescent hybrid materials. These compounds were obtained through Sonogashira coupling reaction and demonstrated UV-A absorption and green-blue fluorescence emission. The mono-silylated BTD compounds were used as precursors for the synthesis of new organic-inorganic hybrid materials through sol-gel reaction, resulting in materials with low BTD content and green-blue fluorescence emission.

DYES AND PIGMENTS (2023)

Article Chemistry, Physical

2,1,3-Benzothiadiazole-based bis-silylated compounds: Synthesis and use in the preparation of highly fluorescent low-contend organic-inorganic hybrid materials

Victoria G. Isoppo, Marieli Oliveira Rodrigues, Fabiano S. Rodembusch, Angelica V. Moro

Summary: Herein, we report the synthesis of bis-silylated 2,1,3-benzothiadiazole derivatives and their application in the preparation of photoactive organic-inorganic hybrid materials. The obtained hybrid materials exhibit high quantum yields and fluorescence emission in the solid state.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2023)

Article Endocrinology & Metabolism

Vitamin D3 improves spatial memory and modulates cytokine levels in aged rats

Tatiani Bellettini-Santos, Michelle Lima Garcez, Francielle Mina, Natalia Quadros Magnus, Nathalia de Souza Pereira, Ariandne de Oliveira Marques, Gabriela Serafim Keller, Gabriel Casagrande Zabot, Natalia Baltazar do Nascimento, Eduarda Behenck Medeiros, Lisienny Campoli Tono Rempel, Ewa Kucharska, Tiago Elias Allievi Frizon, Alexandre Goncalves Dal-Bo, Josiane Budni

Summary: This study aimed to evaluate the effects of vitamin D3 on spatial memory and cytokine levels in geriatric rats. The results showed that vitamin D3 supplementation improved spatial memory in rats aged 6, 13, and 22 months, and it also improved spatial memory in 31-month-old rats at a high dose. The lower dose mainly regulated inflammatory cytokines in the frontal cortex. These findings suggest that vitamin D3 may have an immunomodulatory effect on aging.

METABOLIC BRAIN DISEASE (2023)

Article Chemistry, Applied

Imidazo[1,2-a]pyridine-based hybrids. Copper-catalyzed cycloaddition synthesis, photophysics, docking, and interaction studies with biomacromolecules

Eric F. Lopes, Maiara T. Saraiva, Natali P. Debia, Luana Silva, Otavio A. Chaves, Rafael Stieler, Bernardo A. Iglesias, Fabiano S. Rodembusch, Diogo S. Ludtke

Summary: In this study, the connection between imidazo[1,2-a]pyridines and biologically relevant molecules was investigated. A copper-catalyzed cycloaddition strategy was used to form these connections, utilizing various azides and imidazo[1,2-a]pyridine moieties bearing an alkyne. A total of 8 imidazo[1,2-a]pyridines with a terminal alkyne were synthesized, leading to the synthesis of 27 new hybrid molecules connected by a triazole ring. Additionally, 17 imidazo[1,2-a]pyridines connected to carbohydrate or naturally originated molecules were prepared. Two compounds based on the benzothiazole moiety were selected for fluorescence and binding studies, showing potential as optical sensors for biomacromolecules.

DYES AND PIGMENTS (2023)

Article Chemistry, Physical

Photocatalytic effects on Au@TiO2 confined in BMIm.NTf2 ionic liquid for hydrogen evolution reactions

R. Gustavo J. Chacon, Fabiano S. Rodembusch, Brunno L. Albuquerque, Wellington D. G. Goncalves, Jonder Morais, Daniel L. Baptista, Allan de Moraes Lisboa, Adriano Feil, Dario Eberhardt, Jose Espeso, Jairton Dupont

Summary: In this study, a photocatalytic device based on gold nanoparticles coated with an ionic liquid was developed for hydrogen evolution reactions via methanol photo reforming and photocatalytic water-splitting. The device prepared through magnetron sputtering exhibited direct Au-TiO2 interactions and the presence of the ionic liquid enhanced the photocatalytic performance. The results showed high apparent quantum yield values for hydrogen evolution using the prepared materials.

INTERNATIONAL JOURNAL OF HYDROGEN ENERGY (2023)

Article Chemistry, Multidisciplinary

Influence of starch used in the sol-gel synthesis of ZnO nanopowders

Willians Lopes de Almeida, Lucas Colombo Freisleben, Brenda Camargo Brambilla, Victoria Goulart Isoppo, Fabiano Severo Rodembusch, Vania Caldas de Sousa

Summary: This study presents the synthesis and characterization of ZnO nanoparticles using starch-assisted sol-gel route with corn and potato starches. The botanical source of starch was found to influence the crystallite size and optical properties of the ZnO nanoparticles. The resulting ZnO nanopowders were obtained with sizes of 26 nm and 23 nm (Scherrer method) using corn and potato starches, and 22 nm and 14 nm (Williamson-Hall method) using the same starches, respectively. The band gap energies were estimated to be around 3.05 to 3.08 eV (Tauc method) and 3.36 to 3.38 eV (effective mass model). The results indicate that the type of botanical source used for starch plays a role in the crystallite size and optical properties of ZnO nanopowders obtained through this sol-gel route.

JOURNAL OF NANOPARTICLE RESEARCH (2023)

Article Biochemistry & Molecular Biology

Spectroscopic Insights of an Emissive Complex between 4'-N,N-Diethylaminoflavonol in Octa-Acid Deep-Cavity Cavitand and Rhodamine 6G

Fabiano da Silveira Santos, Elamparuthi Ramasamy, Lilian Camargo da Luz, Vaidhyanathan Ramamurthy, Fabiano Severo Rodembusch

Summary: Excited-state chemistry is crucial in the field and relies on intermolecular communication. This study investigates whether confinement can modify intermolecular communication and its rate. Results show the presence of an emissive complex between DEA3HF@(OA)(2) and R6G, suggesting a static quenching mechanism. The importance of FRET is discarded in these systems.

MOLECULES (2023)

Article Spectroscopy

Effective enantioselective recognition by steady-state fluorescence spectroscopy: Towards a paradigm shift to optical sensors with unusual chemical architecture

Natali P. Debia, Jenifer M. Muller, Paulo F. B. Gonsalves, Fabiano S. Rodembusch, Diogo S. Ludtke

Summary: A series of amino acid-derived 1,2,3-triazoles connected by a triazole-4-carboxylate spacer were studied for enantioselective recognition using steady-state fluorescence spectroscopy. Optical sensing was performed with chiral analytes, and the sensors showed specific interactions and photophysical responses with each pair of enantiomers. DFT calculations confirmed the specific interaction between the fluorophores and the analytes, supporting the observed high enantioselectivity of these compounds.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2023)

Article Spectroscopy

ESIPT-based benzazole-pyromellitic diimide derivatives. A thermal, electrochemical, and photochemical investigation

Tiago E. A. Frizon, Cristian A. M. Salla, Felipe Grillo, Fabiano S. Rodembusch, Viktor S. Camara, Henrique C. Silva, Eduardo Zapp, Eduardo Junca, Fabio Z. Galetto, Angelica M. de Costa, Gabriela J. Pedroso, Antonio A. Chepluki, Sumbal Saba, Jamal Rafique

Summary: This study synthesized new PMDI derivatives through proton-transfer reactions in the excited state (ESIPT). These compounds exhibited absorption maxima in the ultraviolet region and showed redshifted absorptions compared to the non-ESIPT dye. They also displayed fluorescence emissions dependent on solvent polarity and chemical structure, with ESIPT derivatives showing dual fluorescence and a large Stokes shift. The compounds demonstrated good thermal stability and electrochemical properties.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2023)

Article Chemistry, Physical

Imidazole-based optical sensors as a platform for bisulfite sensing and BSA/ HSA interaction study. An experimental and theoretical investigation

Esther R. S. Paz, Victoria G. Isoppo, Fabiola S. dos Santos, Luana A. Machado, Rossimiriam P. de Freitas, Henrique C. Silva, Otavio A. Chaves, Bernardo A. Iglesias, Fabiano S. Rodembusch, Eufranio N. da Silva

Summary: Fluorescent lapachones were synthesized from the natural product lapachol obtained from Tabebuia sp. Photophysical studies showed strong absorption and fluorescence emission in different solvents. The imidazole compounds showed a selective response to bisulfite ions and have potential applications in biological systems. The interaction of these compounds with human or bovine serum albumin was weak, with different binding regions depending on the nature of the previously complexed metabolite or drug.

JOURNAL OF MOLECULAR LIQUIDS (2023)

Article Chemistry, Multidisciplinary

Direct synthesis of TiO2 nanoparticles without heat treatment: Effect of order of addition and precursor/reducing ratio

Silviany Goulart-Goncalves, Mariana de Souza-Pereira, Renata Martins Benetti, Gecica Cardoso Bellettini, Fabio Elyseu, Alexandre Goncalves Dal-Bo, Adriano Michael Bernardin

Summary: This study aimed to synthesize TiO2 nanoparticles for photocatalysis under UV light without further heat treatment. A 2k factorial design was used to evaluate the effect of precursor/reducing agent ratio on the synthesis. TiO2 nanoparticles with large surface area were successfully synthesized via a controlled precipitation method. The synthesized nanoparticles showed comparable photocatalytic activity to commercial TiO2.

JOURNAL OF PHYSICS AND CHEMISTRY OF SOLIDS (2023)

Article Materials Science, Multidisciplinary

Production and Weathering Exposure of Thermochromic Coatings Used as Sensors to Protect Electricity Distribution Systems

Enio Brogni, Rodrigo da Costa Duarte, Rodrigo Cercena, Emerson Colonetti, Michael Peterson, Maykon Cargnin, Alexandre Goncalves Dal-Bo

Summary: In this study, a temperature sensor with a thermochromic coating was developed to effectively monitor the overheating of electronic system components. Experimental results showed that the thermochromic sensors exhibited good performance under artificial weathering conditions, reducing degradation effects in high temperature, light, and salt spray.

MATERIALS RESEARCH-IBERO-AMERICAN JOURNAL OF MATERIALS (2023)

Article Chemistry, Physical

Experimental and theoretical insights on the photophysical properties of ester-substituted indolizines

Marcelo M. Vieira, Bianca T. Dalberto, Nathalia B. Padilha, Henrique C. S. Junior, Fabiano S. Rodembusch, Paulo H. Schneider

Summary: In this report, we synthesized substituted indolizines using ultrasound irradiation in a one-pot and multicomponent strategy, and studied their photophysical properties. The compounds exhibited absorption maxima in the UV-A-violet region and their electronic transitions were related to allowed 1 pi ->pi* transitions. Indolizines showed fluorescence in the violet-to-green region, and the ground and excited states were influenced by the substituents in the indolizine core. The role of solvent in the deactivation of excited states was critical for exploring these compounds as optical sensors for benzene.

JOURNAL OF MOLECULAR STRUCTURE (2024)

Article Chemistry, Applied

Versatile phototheranostic system: Aza-BODIPY-based nanoparticles with B,O-chelated core and diiodine

Leping Chen, Yanfen Wang, Tingyu Shi, Tiantian Ma, Yang Li, Huayu Qiu, Shouchun Yin, Meier Gu

Summary: This study successfully overcame the limitations of the heavy atom effect by introducing iodine atoms and innovatively enhancing the structure while weakening stacking behavior, achieving high efficiency and precision in photodynamic therapy and photothermal therapy.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

Naphthylamine-based ratiometric fluorescence probe with a large Stokes shift for monitoring mitochondrial peroxynitrite

Bingpeng Guo, Honghan Sa, Peng Zhang, Guiwen Hao, Mengyu Li, Qingqing Jiang, Baoying Li, Wei Shu, Changxiang Shao

Summary: The design of ratiometric fluorescence probes with large Stokes shift is of great significance in detecting and imaging target substances in complex organisms. In this study, a novel fluorophore with a large Stokes shift was easily obtained, and a fluorescence probe based on it demonstrated rapid response, high selectivity, and sensitivity towards peroxynitrite. The probe also showed excellent biocompatibility and remarkable mitochondrial targeting ability, making it suitable for proportional imaging of peroxynitrite in living cells and zebrafish.

DYES AND PIGMENTS (2024)

Review Chemistry, Applied

Recent advances in responsive photonic crystals and their applications in anti-counterfeiting solutions for the textile industry

Haidong Huang, Xiaohui Wang, Xinyang Li, Yichen Li, Guojin Liu, Lan Zhou, Jianzhong Shao

Summary: This article introduces the application of responsive photonic crystals in anti-counterfeiting technology, with a focus on the preparation principle, classification, and preparation methods.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

Synthesis of novel carbene dyes and investigation of their dyeing properties and reaction mechanism for various fabrics

Yunpeng Wang, Tao Zhao, Xiaoye Bi, Chencheng Lv

Summary: In this study, three novel carbene dyes were designed to achieve environmentally friendly dyeing processes. The dyes formed covalent bonds with fibers and exhibited good dyeing performance and high color fastness. These findings highlight the potential of the novel carbene dyes in promoting green production in the textile industry.

DYES AND PIGMENTS (2024)

Review Chemistry, Applied

Donor-acceptor type π-conjugated 1,3,5-triazine dyes synthesis and its application in cell imaging and liquid food safety detection

Yizhe Yan, Xiaopei Zhu, Jia-Xin Cao, Yuan He, Shaoqing Li, Jian-Yong Wang

Summary: In this paper, 1,3,5-triazine dyes were successfully synthesized and their photophysical properties were studied. Two probes were selected for further investigation, showing promising applications in various fields.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

One-step synthesis of AIE-active fluorescent cyclomatrix polyphosphazene spheres as drug delivery carriers

Xin Hu, Tongsheng Huang, Lihua Chen, Weifeng Zhu, Fengjie Deng, Xiancai Li, Jianwen Tian, Meiying Liu, Xiaoyong Zhang, Yen Wei

Summary: This study presents the synthesis of fluorescent cyclomatrix polyphosphazene spheres with aggregation-induced emission (AIE) feature and biodegradable potential for controlled drug delivery. The resulting micelles exhibit high water dispersibility, desirable fluorescence performance, and high drug loading capacity. They can effectively release the encapsulated drug in physiological solution and show excellent biological imaging ability and cytotoxicity against cancer cells.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

Eu(III)-based polymeric nanoparticles as dual-emission turn-off sensor for anthrax biomarker detection

Yanzhu Liu, Yanghui Lei, Dongyan Li, Guangkui Li, Dongping Li, Yongxiu Li

Summary: In this study, luminescent lanthanide nanoparticles were synthesized as a dual emission turn-off probe for detecting 2,6-pyridinedicarboxylic acid (DPA) in water. The nanoparticles showed good dispersion and water stability, and achieved low detection limits for DPA. They also exhibited high recoveries in various samples.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

Minimized defective trap sites in perovskite absorber films by coumarin dye for efficient and reliable perovskite solar cells

Jung Jae Do, Jong Ryeol Kwon, Donghan Kim, Jae Woong Jung

Summary: This study presents a defect passivation approach using coumarin dye as a multi-functional passivating agent of perovskite films to boost power conversion efficiency and operating stability of PSCs. The incorporation of coumarin dye improves the film morphology, enhances carrier extraction/transport, and suppresses trap-assisted recombination in the perovskite films. The optimized device demonstrates impressive reliability and practical applicability, maintaining over 90% of its initial PCE after being exposed to continuous indoor lighting irradiation for 2000 hours.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

A novel luminescent Ni(II) coordination compound for highly selective detection of acetylacetone, MnO4-, tetracycline and Ag+ in aqueous systems

Gang Wang, Yu-Chang Wang, Jing Lu, Wen-Fu Yan, Juan Jin, Yuan-Peng Wang, Jia-Jia Zhang, Hui-Jie Zhang, Hao Dong, Xi-Guang Liu

Summary: A new Ni(II) compound with good solid-state fluorescence performance and stability was synthesized, and it showed outstanding detection properties for various substances in aqueous solutions. This compound has the potential to be a multifunctional sensor.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

Iridescent structural colors printing on cellulose fabrics with robust structural coloration

Luyao Wei, Shenglong Shang, Yu Zheng, Jie Liu, Ping Zhu

Summary: This study developed a facile method to create high saturation and durable structural colors on cotton fabrics. The colors are regulated by adjusting the size of magnetic particles and can be conveniently printed on fabrics using photo masks on transparent films.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

Aggregation-induced phosphorescence emission-active heteroleptic Ir(III) complexes: Synthesis, photophysics, and latent fingerprint detection applications

Zhao Jiang, Qing Zhang, Zhaoyu Kong, Ruijie Qiao, Zichuan Liu, Linzhou Song, Senqiang Zhu, Rui Liu, Hongjun Zhu

Summary: Three heteroleptic Ir(III) complexes with different electron-donating aryl groups were synthesized and their optical properties were investigated. It was found that all three complexes exhibited aggregation-induced phosphorescence emission (AIPE) behaviors, and the relationship between the size of organic ligands and AIPE behaviors was characterized. Ir-PhCz showed the best imaging of latent fingerprints due to its green light emission and high quantum yield.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

A novel thioketal containing fluorescent dye for mercury(II) detection via Hg2+-triggered ACQ to AIE transformation

Zhijun Ruan, Chunxia Fan, Xuanrong Wang, Dong Shao, Xiaodong Yang, Wentao He, Tao Xu, Junqi Lin, Zhengfang Tian

Summary: A novel thioketal-based probe has been designed for rapid and accurate detection of mercury (II) ions, showing different fluorescence characteristics in various states. The probe exhibits excellent selectivity and specificity, making it suitable for Hg2+ detection in water solutions.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

The first BOAHY-based probe for ClO- : Synthesis, spectral investigations and selective recognition behaviour

Jianjun Huang, Xuan Zhao, Daniel Escudero, Luc Van Meervelt, Dongbin Zheng, Yuyu Fang, Wim Dehaen

Summary: A series of BOAHY compounds were successfully synthesized and showed versatile applications as a platform for designing novel fluorescent probes, especially in selective recognition.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

Core-fluorinated dipyrromethanes and BODIPYs. Synthesis and study of photophysical properties

Roman V. Larkovich, Victoria E. Shambalova, Savva A. Ponomarev, Alexander S. Aldoshin, Boris N. Tarasevich, Konstantin A. Lyssenko, Valentine G. Nenajdenko

Summary: An efficient synthetic protocol for the preparation of novel 1,7-difluorinated BODIPYs was elaborated. Their photophysical properties were studied and the effect of 2,6-substituents was evaluated using DFT calculations.

DYES AND PIGMENTS (2024)

Article Chemistry, Applied

19F NMR-based lithium sensors with fluoronaphthalene crown ethers

Haneul Kim, Byungjin Koo

Summary: In this study, a lithium ion sensing methodology based on fluorinated naphthalene compounds using 19F NMR and UV-vis spectroscopy is reported. The binding of lithium ions to the compounds is confirmed by changes in chemical shifts and peak broadening. Additionally, the effect of different crown ether ring sizes on the binding ability is observed. This study provides a new method for lithium ion sensing using spectroscopy.

DYES AND PIGMENTS (2024)