4.7 Article

Luminescent organoboron compounds derived from salicylidenebenzohydrazide: Synthesis, characterization, structure, and photophysical properties

期刊

DYES AND PIGMENTS
卷 99, 期 3, 页码 1036-1043

出版社

ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2013.07.039

关键词

Boron; Fluorescent; Salicylidenebenzohydrazide; X-ray; B-11-NMR; Organic materials

资金

  1. CONACYT [156450]
  2. PAICYT-UANL [CN886-11]
  3. CONACYT

向作者/读者索取更多资源

A series of substituted 2-hydroxysalicylidine benzohydrazides were converted into their phenyl-boron complexes in good yields upon reaction with phenylboronic acid. All new compounds were characterized by NMR, UV, IR, spectroscopy and mass spectrometry. The X-ray structures of two complexes demonstrate that the boron atoms adopt a tetrahedral geometry. The B-11 NMR chemical shifts of the boron atom in the complexes are also consistent with the presence of tetracoordinate boron centres. The photophysical properties of the free benzohydrazide ligands and their boron complexes have been determined and display quantum yields below 1% with lifetimes in the range 10(-10)-10(-11) s. (C) 2013 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, Inorganic & Nuclear

Relativistic modulation of supramolecular halogen/copper interactions and phosphorescence in Cu(i) pyrazolate cyclotrimers

Zhou Lu, Mukundam Vanga, Shan Li, Joseph O. O. Adebanjo, Monika R. R. Patterson, H. V. Rasika Dias, Mohammad A. A. Omary

Summary: This study explores the synthesis, structure, and photophysics of a cyclic trinuclear copper(i) complex with iodine substitution, Cu-3[4-I-3,5-(CF3)(2)Pz](3), in comparison with previously reported complexes containing 4-Br/4-Cl groups. The crystal structure is stabilized by various supramolecular interactions, including Cu3MIDLINE HORIZONTAL ELLIPSISI and hydrogen/halogen bonding. Experimental and computational investigations are conducted to study the photophysical properties and supramolecular interactions of all three 4-halo complexes in relation to relativistic effects.

DALTON TRANSACTIONS (2023)

Article Chemistry, Inorganic & Nuclear

Copper(I), Silver(I), and Gold(I) Ethylene Complexes of Fluorinated and Boron-Methylated Bis- and Tris(pyridyl)borate Chelators

Brandon T. Watson, Mukundam Vanga, Anurag Noonikara-Poyil, Alvaro Munoz-Castro, H. V. Rasika Dias

Summary: Bis-and tris-pyridyl borate ligands with pyridyl donor arms, a methylated boron cap, and a fluorine-lined coordination pocket have been synthesized and used in coinage metal chemistry. These ligands allowed for the isolation of group 11 metal-ethylene complexes, with gold complexes showing the largest coordination-induced upfield shifts of the ethylene 13C resonance. Solid-state structures of these complexes revealed the rare K2 coordination mode instead of the typical K3 coordination mode. Computational analyses indicated the favored K2 coordination mode and the strong interaction between gold(I) and ethylene.

INORGANIC CHEMISTRY (2023)

Article Chemistry, Physical

Boronate derivatives of damnacanthal: Synthesis, characterization, optical properties and theoretical calculations

David Caceres-Castillo, Gumersindo Miron-Lopez, Maria C. Garcia-Lopez, Rodrigo Chan-Navarro, Ramiro F. Quijano-Quinones, Flor M. Briceno-Vargas, Roger Cauich-Kumul, Hugo Morales-Rojas, Angel D. Herrera-Espana

Summary: The natural anthraquinone Damnacanthal (1) was isolated from the roots of Morinda panamensis and used as a building block to construct five fluorescent boronate derivatives. The optical properties of the derivatives were characterized, and it was found that the substituents on the phenyl group attached to the boron atom influenced their emission wavelength and fluorescence quantum yield.

JOURNAL OF MOLECULAR STRUCTURE (2023)

Article Chemistry, Physical

Green synthesis of BOSCHIBAs: Photo- and water stability, cytotoxicity assays, and theoretical calculations

Areli A. Molina-Paredes, Victor M. Jimenez Perez, Marcos R. Bahena-Villarreal, Mario Sanchez, Azael A. Cavazos-Jaramillo, Juan M. Alcocer-Gonzalez, Alma Saucedo-Yanez, Casiano del Angel Mosqueda, Jesus A. Lara-Ceron, Blanca M. Munoz Flores

Summary: In this study, three boron compounds were synthesized by microwave-assisted synthesis and multicomponent reaction. The photophysical properties, photostability, and stability in aqueous media of all compounds were evaluated. Compound 1 with tert-butyl groups showed high photostability and water-stability, making it suitable as a fluorescent biomarker for biomedical applications.

JOURNAL OF MOLECULAR STRUCTURE (2023)

Article Materials Science, Multidisciplinary

p-Phenyleneethynylene copolymer CdS quantum dot Superstructures. Synthesis, photophysics and vesicle formation

Marcos Joaquin Guillen, Erick Alfonso, Ivana Moggio, Eduardo Arias, Geraldina Rodriguez, Raquel Ledezma, Matthew Espe, Luis Yate, Ronald Ziolo

Summary: In this study, CdS QDs were synthesized using MPS as ligand and mixed with an amphiphilic p(phenyleneethynylene) copolymer coPE, resulting in CdS(MPS)-coPE, a material with spherical superstructures and stability, especially in spun films. The unique supramolecular behavior of CdS(MPS)-coPE could be potentially utilized for host-guest white light emission or biosensing.

MATERIALS SCIENCE AND ENGINEERING B-ADVANCED FUNCTIONAL SOLID-STATE MATERIALS (2023)

Article Chemistry, Organic

The Stereoselective Total Synthesis of the Elusive Cephalosporolide F

Leonardo Xochicale-Santana, Omar Cortezano-Arellano, Bernardo A. Frontana-Uribe, Victor M. Jimenez-Perez, Fernando Sartillo-Piscil

Summary: Here we describe the total synthesis of (+)-cephalosporolide F using a protecting-group-free approach. The key steps in this process include a microwave-assisted reaction between Meldrum's acid and D-glucose to create an octono-1,4-lactone derivative, as well as a low temperature visible-light photoredox spirocyclization reaction to form ceph F. These environmentally friendly methods allowed the successful completion of this challenging synthesis.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Materials Science, Multidisciplinary

New non-conjugated luminescent glycol-terephthalate oligomers bearing aryl Schiff bases: Chemical functionalization, chemical-optical characterization, thermal behavior and fluorescent sensing properties

Carlos H. Flores-Tamez, Perla Elizondo-Martinez, Rosa M. Jimenez-Barrera, Ivana Moggio, Eduardo Arias, Maria G. Sanchez-Anguiano, Maria C. Garcia-Lopez, Rodrigo Chan-Navarro

Summary: New non-conjugated luminescent glycol-terephthalate oligomers were synthesized by a free radical reaction with aryl Schiff bases, which proved to be a superior method compared to ionizing or plasma treatments in terms of processing facility and reproducibility. The compounds were characterized by various techniques, and their thermal behavior and optical properties were investigated. The anthracenyl oligomer exhibited good linearity in a carbon dioxide sensing test, making this the first report on luminescent glycol-terephthalate oligomers for carbon dioxide sensing.

OPTICAL MATERIALS (2023)

Article Chemistry, Physical

Synthesis and Study of the Optical Properties of a Conjugated Polymer with Configurational Isomerism for Optoelectronics

Oscar Javier Hernandez-Ortiz, Damaris Castro-Monter, Ventura Rodriguez Lugo, Ivana Moggio, Eduardo Arias, Maria Isabel Reyes-Valderrama, Maria Aurora Veloz-Rodriguez, Rosa Angeles Vazquez-Garcia

Summary: A p-conjugated polymer (PBQT) containing BDT units alternated with a quinoline-vinylene trimer was synthesized via the Stille reaction. The chemical structure was confirmed by NMR, FT-IR, and MALDI-TOF. PBQT exhibited photochromism and fluorescence change, making it suitable for optical sensors or switches. The polymer also showed potential for photovoltaic applications with its good energetic match and absorption properties.

MATERIALS (2023)

Article Chemistry, Multidisciplinary

Classical Gold Carbonyl Complexes in Tetrahedral and Trigonal-Planar Settings

Mukundam Vanga, Alvaro Munoz-Castro, H. V. Rasika Dias

Summary: A unique four-coordinate, classical gold(I)-carbonyl complex with substantial backdonation from gold has been isolated using a special ligand. The study of its lighter analogs of silver(I) and copper(I) enabled the investigation of trends in the coinage-metal family. Computational analysis revealed multiple components in the AuI-CO bonds. The complexes with the special ligand displayed remarkably low C-O stretching frequencies.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

Article Chemistry, Inorganic & Nuclear

Thallium(I) Complexes of Tris(pyridyl)borates and a Comparison to Their Pyrazolyl Analogues

Mukundam Vanga, Vo Quang Huy Phan, Jiang Wu, Alvaro Munoz-Castro, H. V. Rasika Dias

Summary: Thallium(I) complexes of B-methylated and B-phenylated tris(pyridyl)borates with trifluoromethyl groups at the pyridyl ring 6-positions have been synthesized and compared to the tris(pyrazolyl)borate analogues. The coordination modes and spectroscopic features of these complexes have been studied, revealing distinct differences between the two scorpionate families. The steric demands of the ligands have been quantified using the buried volume concept. Ligand transfer chemistry from these complexes to copper(I) under ethylene has also been investigated, and computational analyses of the coordination modes have been performed.

INORGANIC CHEMISTRY (2023)

Correction Chemistry, Organic

Total Synthesis of (+/-)-Calcaridine A and (+/-)-epi-Calcaridine A (vol 10, pg 5055, 2008)

Panduka B. Koswatta, Rasapalli Sivappa, H. V. Rasika Dias, Carl J. Lovely

ORGANIC LETTERS (2023)

Article Polymer Science

Silver Nanoparticle-PEDOT:PSS Composites as Water-Processable Anodes: Correlation between the Synthetic Parameters and the Optical/Morphological Properties

Stefania Zappia, Marina Alloisio, Julio Cesar Valdivia, Eduardo Arias, Ivana Moggio, Guido Scavia, Silvia Destri

Summary: The properties of silver nanoparticles synthesized in situ within commercial PEDOT:PSS formulations were systematically investigated. The reagent ratio was found to be the only parameter affecting the properties of the nanoparticles. The stabilization of the nanoparticles occurred mainly in PEDOT:PSS domains with low silver content, while in domains with high silver content, the particles formed and perturbed the absorption of the conjugated polymer. Furthermore, an optimized film morphology was used to fabricate a water-processable anode.

POLYMERS (2023)

Article Chemistry, Multidisciplinary

Rotors of BOSCHIBAs as endoplasmic reticulum fluorescent probes in HeLa and human umbilical vein endothelial cells

Margarita Lopez-Espejel, Marisol Ibarra-Rodriguez, Blanca M. Munoz-Flores, Marcos R. Bahena-Villarreal, Azael A. Cavazos-Jaramillo, Monica D. Garza-Villegas, Cristina Rodriguez-Padilla, Itza E. Luna-Cruz, H. V. Rasika Dias, Juan M. Alcocer-Gonzalez, Victor M. Jimenez-Perez

Summary: The fluorescence imaging technique is widely used in natural and life sciences, but current commercial biomarkers have several disadvantages. In this study, two new fluorescent molecular rotors (SB-B2 and SB-B23) derived from Boron Schiff bases (BOSCHIBAs) were synthesized and characterized. The crystal structure of SB-B23 showed a binuclear complex. Both compounds exhibited viscochromic and thermochromic properties. These low cytotoxicity BOSCHIBAs showed selective fluorescent staining of the endoplasmic reticulum in HeLa cells and HUVECs.

NEW JOURNAL OF CHEMISTRY (2023)

Article Chemistry, Inorganic & Nuclear

Filling the gap with a bulky diaryl boron group: fluorinated and non-fluorinated copper pyrazolates fitted with a dimesityl boron moiety on the backbone

Mukundam Vanga, Benjamin T. Diroll, Alvaro R. Munoz-Castro, H. V. Rasika Dias

Summary: Successful synthesis of sterically demanding diarylboron derivatives and their corresponding copper pyrazolate complexes with modulated photophysical properties is reported in this study. The introduction of secondary diarylboron luminophores and adjustment of the supporting ligand steric features allows for the modulation of the metal pyrazolate's photophysical properties. Computational analysis of the structures and photophysical properties of copper complexes is also presented.

DALTON TRANSACTIONS (2023)

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)