New Coumarin-benzoxazole derivatives: Synthesis, photophysical and NLO properties

Sun, Jian; Zheng, Mingming; Jia, Jianhong; Wang, Wenbiao; Cui, Yanhong; Gao, Jianrong

doi:10.1016/j.dyepig.2019.01.010

Cited by 35 publications

(10 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is known, for example, that crystals of some BZ-naphthalene derivatives exhibit photomechanical effect [104]. The conjugation with coumarins gives access to compounds with valuable non-linear optic (NLO) properties [105], while cyanines derivatives are NIR-emitting bio-probes [106]. There are many things to explore in the field of closely-related compounds, such as benzothiadiazole derivatives, which exhibit reversible mechanofluorochromism [107] and multi-stimuli responsiveness [108].…”

Section: Discussionmentioning

confidence: 99%

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Fery–Forgues

Vanucci-Bacqué

2021

Top Curr Chem (Z)

View full text Add to dashboard Cite

Molecules that exhibit solid-state luminescence enhancement, i.e. the rare property to be more strongly emissive in the solid state than in solution, find an increasing number of applications in the fields of optoelectronic and nanophotonic devices, sensors, security papers, imaging and theranostics. Benzazole (BZ) heterocycles are of particular value in this context. The simple enlargement of their πelectron system using a -C=C-Ar, or -N=C-Ar moiety is enough for intrinsic SLE properties to appear. Their association with a variety of polyaromatic motifs leads to SLE-active molecules that frequently display attractive electroluminescent properties and are sensitive to mechanical stimuli. The excitedstate intramolecular proton transfer (ESIPT) process that takes place in some hydroxy derivatives reinforces the SLE effect and allows the development of new sensors based on a protection/deprotection strategy. BZ may also be incorporated into frameworks that are prototypical aggregation-induced enhancement (AIE) luminogens, such as the popular tetraphenylethene (TPE), leading to materials with excellent optical and electroluminescent performance. This review encompasses the various ways to use benzazole units in SLE systems. It underlines the significant progresses recently made in the understanding of the photophysical mechanisms involved. A brief overview of the synthesis shows that BZ units are robust building blocks, easily incorporated into a variety of structures. Generally speaking, we try to show how advantage may be taken from these small heterocycles for the design of increasingly efficient luminescent materials.

show abstract

Section: Discussionmentioning

confidence: 99%

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Fery–Forgues

Vanucci-Bacqué

2021

Top Curr Chem (Z)

View full text Add to dashboard Cite

show abstract

“…In this study, we prepared a fluorescent probe based on coumarin and furan‐2‐carbohydrazide using the Schiff base reaction (Scheme ). Coumarin is an excellent fluorophore with high fluorescence quantum yield, good optical stability, low toxicity and ease of preparation; furan‐2‐carbohydrazide is well provided with coordination sites. This probe showed favourable specificity and sensitivity, and a capability for fluorescence imaging in living cells.…”

Section: Introductionmentioning

confidence: 96%

A highly selective aggregation‐induced emission fluorogen for sensitive detection of Al³⁺ in living cells

Xie

Yan

et al. 2019

Luminescence

View full text Add to dashboard Cite

A Schiff's base derivative was synthesized using a condensation reaction between 8formyl-7-hydroxy-4-methylcoumarin and furan-2-carbohydrazide that produced marked aggregation-induced emission and had excellent ability to specifically recognize aluminium ions (Al 3+ ). This compound displayed faint fluorescence in the benign solvent dimethyl formamide, and exhibited obvious green fluorescence following addition of specific amounts of water. Moreover, it exhibited strong blue fluorescence after combination with Al 3+ even in the presence of other interfering ions.These experimental results demonstrated that this derivative could be used as a fluorescence probe for Al 3+ . The advantages, including significant fluorescence change, high selectivity and sensitivity, and fast response, meant that this probe could be used both to detect Al 3+ in water samples and for fluorescence imaging in living cells.

show abstract

“…8 Similarly, the widely employed electron acceptors exhibit negative mesomeric or inductive effect (-M/-I) that comprise of -NO 2 , -CN, -CHO, -COOH groups as well as heterocycles such as pyridine, imidazoles, benzothiazoles, benzooxazoles and many others. 8 Pushpull chromophores containing the heterocyclic coresoxazoles, [15][16][17][18][19] oxadiazoles [20][21][22][23] and triazoles 24,25 have received much attention in recent years, however, studies on the photophysical and NLO properties of the related tetrazole-based molecular systems are scarce in the literature. For instance, photophysical properties of compounds containing a tetrazole scaffold have been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, photophysical and nonlinear optical properties of push–pull tetrazoles

et al. 2022

View full text Add to dashboard Cite

show abstract

New Coumarin-benzoxazole derivatives: Synthesis, photophysical and NLO properties

Cited by 35 publications

References 43 publications

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

A highly selective aggregation‐induced emission fluorogen for sensitive detection of Al³⁺ in living cells

Synthesis, photophysical and nonlinear optical properties of push–pull tetrazoles

Contact Info

Product

Resources

About

New Coumarin-benzoxazole derivatives: Synthesis, photophysical and NLO properties

Cited by 35 publications

References 43 publications

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

A highly selective aggregation‐induced emission fluorogen for sensitive detection of Al3+ in living cells

Synthesis, photophysical and nonlinear optical properties of push–pull tetrazoles

Contact Info

Product

Resources

About

A highly selective aggregation‐induced emission fluorogen for sensitive detection of Al³⁺ in living cells