Brønsted acid promoted addition–cyclization and C–C bond cleavage: a convenient synthesis of 2-amino-5-aroylmethylthiazoles derivatives

Ni, Fan; Yang, Yan; Shu, Wen‐Ming; Ma, Junrui; Wu, An‐Xin

doi:10.1039/c4ob01519c

Cited by 20 publications

(12 citation statements)

References 48 publications

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“…Research and development of organic fluorescent molecules has been a focus area of interdisciplinary chemistry research for long, due to their wide‐ranging applications in optoelectronic devices, fluorescence sensing and bioimaging [1a–k] . These fluorophores exhibit two main structural characteristics which impact their photophysical properties: (1) presence of a planar and rigid framework having an extended π‐conjugated system [2] .…”

Section: Introductionmentioning

confidence: 99%

Amino‐Terephthalonitrile‐Based Single Benzene Fluorophores with Large Stokes Shifts and Solvatochromic Behavior

Raghava

Chattopadhyay

Bhavana

et al. 2023

Chemistry An Asian Journal

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We have synthesized a small library of blue‐to‐green emissive single benzene‐based fluorophores (SBFs) in a short synthetic sequence. The molecules exhibit good Stokes shift in the range of 60–110 nm and select examples also possess very high fluorescence quantum yields of up to 87%. Theoretical investigations into the ground state and excited state geometries of many of these compounds reveal that good degree of planarization between the electron donor secondary amines and electron accepting benzodinitrile units can be achieved under certain solvatochromic conditions, giving rise to the strongly fluorescent behavior. On the other hand, the excited state geometry which lacks co‐planarity of the donor amine and the single benzene moiety can open up a non‐fluorescent channel. Additionally, in molecules with a dinitrobenzene acceptor, the perpendicular nitro moieties render the molecules completely non‐emissive.

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Section: Introductionmentioning

confidence: 99%

Amino‐Terephthalonitrile‐Based Single Benzene Fluorophores with Large Stokes Shifts and Solvatochromic Behavior

Raghava

Chattopadhyay

Bhavana

et al. 2023

Chemistry An Asian Journal

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“…Fluorophores with planar structures can easily aggregate, leading to fluorescence quenching. 11 12 The introduction of spatially site-resistant groups to the molecule can prevent it from aggregating, thereby improving its dispersibility. But at the same time, the introduction of site-resistant groups also brings a certain degree of flexibility.…”

Section: Ecx Dyes Based On a Carbon-bridged Spiro Ring Strategymentioning

confidence: 99%

New High-Performance Fluorescent Dye Scaffolds: Applications for Bioimaging and Biosensing

Cheng

Lei

2023

Synlett

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Fluorescence imaging in the short-wave infrared region (SWIR, 850-2500 nm) window has become an indispensable tool in biomedical research with weaker absorption, less light scattering, and less background fluorescence in this window. As we know, the design and synthesis of fluorescent dyes and fluorescent probes are the cores of fluorescence imaging and biosensing. Thus, their photophysical mechanisms exploring and bioanalytical applications are multidisciplinary and cutting-edge research topics. In this regard, we have been working on high-performance fluorescent dyes and fluorescent probes for years. In short, we have developed a series of bright, stable, aggregation-resistant, SWIR fluorescent dyes ECXs, based on a carbon-bridged spiro ring strategy. Besides, we also developed a series of high-performance SWIR fluorescent dyes CXs and Chrodols, which combine the structural advantages of cyanine and xanthenoid dyes. Based on these new SWIR scaffolds, we further constructed some activatable SWIR fluorescent probes with OFF-ON or ratiometric properties for biosensing in vivo. Therefore, the mainline of our work is to deeply understand the photophysical mechanisms of fluorescent dyes, to create high-performance luminescent dyes, and further develop fluorescent probes for bioimaging and biosensing.

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“…[ 33–36 ] BODIPY has high photostability, chemical stability, and high fluorescence yield in dark cell background, making it an excellent candidate for synthesizing probes. [ 37–38 ] BODIPY based probes have been highly effective in detecting ROSs in mitochondria for several reasons. First, BODIPY exhibits low toxicity, making it compatible with mitochondrion, which is a fragile organelle in the cell.…”

Section: Introductionmentioning

confidence: 99%

Mitochondria‐Targeting BODIPY Probes for Imaging of Reactive Oxygen Species

Sun

Tang

et al. 2023

Advanced Sensor Research

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Reactive oxygen species (ROSs) are an important class of signaling molecules that play a critical role in regulating physiological processes in the human body. Mitochondria are the primary site of ROSs production, and abnormal concentrations of ROSs can lead to the malignant proliferation of cells, resulting in diseases. Therefore, it is crucial to detect ROSs in mitochondria. Fluorometric methods have gained significant attention from scientists because of their ease of observation, simplicity of operation, and noninvasiveness. Among the fluorescent dyes, boron‐dipyrromethene (BODIPY) stands out for its high quantum yield, large molar extinction coefficient, and excellent chemical stability, making it widely used in fluorescent imaging. The common design principle of fluorescent probe for the detection of ROSs includes photo‐induced electron transfer, intramolecular charge transfer, and fluorescence resonance energy transfer. This paper provides an overview of BODIPY‐based fluorescent probes designed for imaging ROSs in mitochondria, covering the sensing mechanisms, molecular engineering strategies, and recent advancements. Additionally, the review provides insight into the potential clinical applications of mitochondria‐targeting BODIPY probes in disease diagnosis.

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Brønsted acid promoted addition–cyclization and C–C bond cleavage: a convenient synthesis of 2-amino-5-aroylmethylthiazoles derivatives

Cited by 20 publications

References 48 publications

Amino‐Terephthalonitrile‐Based Single Benzene Fluorophores with Large Stokes Shifts and Solvatochromic Behavior

Amino‐Terephthalonitrile‐Based Single Benzene Fluorophores with Large Stokes Shifts and Solvatochromic Behavior

New High-Performance Fluorescent Dye Scaffolds: Applications for Bioimaging and Biosensing

Mitochondria‐Targeting BODIPY Probes for Imaging of Reactive Oxygen Species

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