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Coumarin-based two-photon AIE fluorophores: Photophysical properties and biological application

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Chinese Chemical Letters 2023年第4期34卷 231-235页

作者： Yitong Yang Hao Zhong Benhua Wang Xiaojie Ren Xiangzhi Song College of Chemistry and Chemical Engineering Central South UniversityChangsha 410083China Department of Chemistry and Center of Super-Diamond and Advanced Films(COSDAF) City University of Hong KongHong Kong 999077China

Based on the coumarin skeleton, we deliberately designed two groups of fluorophores, termed as CoumR and Naph-Coum-R, using the diphenylamino group as the electron donor, which displayed longwavelength emissions(red spectral region), large Stokes shift(up to 204 nm), superior AIE performance,and large two-photon absorbance cross-sections(as high as 365 GM). The electron-withdrawing substituents at the 3-position of these dyes could induce a significant red-shift in their emission spectra.Preliminary imaging experiments demonstrated the capability of these dyes as two-photon fluorophores for specifically staining lipid droplets in living cells.

关键词： fluorescent dyes AIE Two-photon Large Stokes shifts Lipid droplets

Development of environment-insensitive and highly emissive BODIPYs via installation of N,N'-dialkylsubstituted amide at meso position

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Chinese Chemical Letters 2022年第9期33卷 4175-4178页

作者： Junping Bai Junliang Zhou Xin Ji Nannan Wang Xiaochun Dong Wei Wu Weili Zhao School of Pharmacy Institutes of Integrative MedicineFudan UniversityShanghai 201203China Key Laboratory for Special Functional Materials of Ministry of Education School of Materials Science and EngineeringHenan UniversityKaifeng 475004China

fluorescent dyes play a crucial role in fluorescence imaging and sensing technology.However,there is a dilemma that they are usually intrinsically hydrophobic which lacks of emission in water and modification with ionic groups to access water solubility may result in poor membrane permeability.fluorescent dyes with strong fluorescence emission in both nonpolar and polar solvents are highly desirable.In this manuscript,we reported a strategy to develop fluorescent BODIPY dyes via installation of amide moiety at meso position of 1,3,5,7-tetramethyl-BODIPY and discovered that N,N'-dialkylsubstituted BODIPY amides possessed highly fluorescent emission with favorable environment-insensitive properties.

关键词： fluorescent dyes BODIPY Environment-insensitive Bioimaging

Better understanding of the activated sludge process combining fluorescence-based methods and flow cytometry:A case study

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Journal of Environmental Sciences 2020年第4期32卷 51-58页

作者： Vanesa Benito Javier Etxebarria Felipe Goni-de-Cerio Inigo Gonzalez Pilar Brettes Ana Urkiaga GAIKER Parque TecnológicoEd.20248170ZamudioBizkaiaSpain EDAR Galindo Bilbao Bizkaia Water ConsortiumSestao 48910BizfcaiaSpain

This study aims to demonstrate the validity of fluorescence-based methods,together with flow cytometry,as a complementary tool to conventional physicochemical analyses carried out in wastewater treatment plants(WWTPs),for the control of the currently largely unknown activated sludge process.Staining with SYTO 9,propidium iodide and 5-(and 6)-carboxy-2’,7’-difluorodihydrofluorescein diacetate(carboxy-H2 DFFDA)was used for cell viability and oxidative stress monitoring of the bacterial population forming the activated sludge of a WWTP.Throughout the period of research,several unstable periods were detected,where the non-viable bacteria exceeded the 75%of the total bacterial population in the activated sludge,but only in one case the cells with oxidative stress grew to 9%,exceeding the typical values of2%-5%of this plant.These periods coincided in two cases with high values of total suspended solids(SST)and chemical oxygen demand(COD)in the effluent,and with an excess of ammonia in other case.A correlation between flow cytometric and physicochemical data was found,which enabled to clarify the possible origin of each case of instability in the biological system.This experience supports the application of bacterial fluorescence staining,together with flow cytometric analysis,as a simple,rapid and reliable tool for the control and better understanding of the bacteria dynamics in a biological wastewater treatment process.

关键词： Activated sludge Wastewater treatment Cell viability Oxidative stress fluorescent dyes Flow cytometry

Stimuli-responsive organic chromic materials with near-infrared emission

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Chinese Chemical Letters 2018年第10期29卷 1429-1435页

作者： Weijie Chen Yingle Pan Jianhua Chen Fengying Ye Sheng Hua Liu Jun Yin Key Laboratory of Pesticide and Chemical Biology Ministry of EducationCollege of ChemistryCentral China Normal University

Organic chromic materials that respond to external stimuli, especially in the solid state, have sparked extensive interest owing to their potential use as smart materials. In particular, the availability of chromic materials, which emit fluorescence or phosphorescence in the deep penetrating, near-infrared（NIR）region, has led to great improvements in imaging. Various methods that were commonly applied to construct chromic materials, have been reformed to develop the novel type of compounds, and some have received rewards with excellent fingdings. Relevant research achievements of practical applications have showed their potential with the changes that locate in the NIR region, while further in-depth explorations about the inherent chromic chromism are underway. In this review, several representative studies, which have led the development of responsive organic chromic materials with near-infrared emission, will be discussed.

关键词： Stimuli-response Near-infrared emission fluorescent dyes Chromic materials Mechanochromism

Novel Water Soluble fluorescent Trimethine Indocyanines Containing N-ρ-Carboxybenzyl Group

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Chinese Chemical Letters 2003年第1期14卷 22-24页

作者： Li Qiu WANG Xiao Jun PENG Rong ZHANG Guo Quan XU Jing Nan CUI State Key Laboratory of Fine Chemicals Dalian University of TechnologyDalian 116012

Two fluorescent indocyanine dyes containing at least one p-carboxybenzyl group on the nitrogen atoms in the heterocyclic rings were designed and synthesized. Their absorption maxima were 549 nm and 551 nm in water re... 详细信息

关键词： Sulfoindocyanine fluorescent dyes biological label.

Rational design of far red to near-infrared rhodamine analogues with huge Stokes shifts for single-laser excitation multicolor imaging

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Chinese Chemical Letters 2021年第12期32卷 3890-3894页

作者： Xingxing Zhang Tianbing Ren Feiyu Yang Lin Yuan State Key Laboratory of Chemo/Biosensing and Chemometrics College of Chemistry and Chemical EngineeringHunan UniversityChangsha 410082China

Rhodamine dyes have been widely employed in biological imaging and sensing. However, it is always a challenge to design rhodamine derivatives with huge Stokes shift to address the draconian requirements of single-excitation multicolor imaging. In this work, we described a generally strategy to enhance the Stokes shift of rhodamine dyes by completely breaking their electronic symmetry. As a result, the Stokes shift of novel rhodamine dye DQF-RB-Cl is up to 205 nm in PBS, which is the largest in all the reported rhodamine derivatives. In addition, we successfully realized the single excitation trichromatic imaging of mitochondria, lysosomes and cell membranes by combining DQF-RB-Cl with commercial lysosomal targeting probe Lyso-Tracker Green and membrane targeting dye Dil. This is the organic synthetic dyes for SLE-trichromatic imaging in cells for the first time. These results demonstrate the potential of our design as a useful strategy to develop huge Stokes shift fluorophore for bioimaging.

关键词： fluorescent dyes Rhodamine analogues Huge stokes shifts Single-laser excitation Multicolor imaging

Progress of Optically Encoded Microspheres for Multiplexed Assays

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Journal of Shanghai Jiaotong university(Science) 2014年第5期19卷 521-530页

作者：朱莹徐宏古宏晨 School of Biomedical Engineering Shanghai Jiaotong University

New initiatives put forward by clinical diagnosis require the development of technologies for high throughput screening(HTS) of multiple analytes. Suspension arrays have great advantages over the planar arraybased multiplexing assays, and the encoded bead is the key for providing multiplexing capability. Among various encoding strategies, optically encoded microspheres have been widely used while the number of codes is still limited. This review discusses the progress of optical encoding strategy from mainly three aspects, namely organic dyes, quantum dots(QDs) and surface-enhanced Raman scattering(SERS) active substrates. Emphases are put up on describing how these optical encoded microbeads are manufactured and the merits and demerits of different encoding materials are compared.

关键词： multiplexing suspension arrays optically encoded microspheres fluorescent dyes quantum dots(QDs) surface-enhanced Raman scattering(SERS)

New fluorescent Conjugates Displaying Solvatochromic Properties

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Chinese Journal of Chemistry 2017年第5期35卷 707-715页

作者： Huijing Liu Rongrong Huang Yu Fang Key Laboratory of Applied Surface and Colloid Chemistry (Ministry of Education) School of Materials Science and Engineering Shaanxi Normal University Xi'an Shaanxi 710062 China School of Chemistry and Chemical Engineering Shaanxi Normal University Xi 'an Shaanxi 710062 China

Four new fluorescent dyes based on bis（phenyl-ethynyl-）-2-naphthyl （BPEN） were designed and synthesized.To improve the solvatochromic property and enhance the brightness of the fluorescent BPEN,an electron-donatin... 详细信息

关键词： SOLVATOCHROMISM FLUORESCENCE yield fluorescent dyes NAPHTHYL compounds ELECTRON donor-acceptor complexes AZETIDINE