Recent progress on the synthesis of henna-based dibenzoxanthenes

Sadeghpour, Mahdieh; Olyaei, Abolfazl; Adl, Alireza

doi:10.1039/d1nj02475b

Cited by 10 publications

(4 citation statements)

References 61 publications

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“…[45,46,51] Many strategies have been employed to shift the emission of xanthene dyes towards deep red to the NIR region and to have larger Stokes shift. [41,52,[61][62][63][64][53][54][55][56][57][58][59][60] A well-known strategy is to form a xanthene hybrid by combing xanthene derivatives with other fluorophores. [60,61] One of the advantages of this strategy is that the resulting hybrid fluorophore retains the advantageous properties of the individual fluorophores.…”

Section: Xanthene Dyesmentioning

confidence: 99%

“…The disadvantage of the xanthene dyes is that the emission and Stokes shift of the classical xanthene dyes is ≤600 nm and∼ 34 nm, respectively, which restrict their use in the biological application [45,46,51] . Many strategies have been employed to shift the emission of xanthene dyes towards deep red to the NIR region and to have larger Stokes shift [41,52,61–64,53–60] . A well‐known strategy is to form a xanthene hybrid by combing xanthene derivatives with other fluorophores [60,61] .…”

Section: Introductionmentioning

confidence: 99%

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Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

Khan

Sekar

2023

ChemistrySelect

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Xanthene dyes exhibit remarkable photophysical properties and photostability. Their ability to switch fluorescence on/off depending on the external environment makes them a promising candidate for imaging/sensing/tracking/labeling probes. However, their emission � 600 nm and Stokes shift ∼ 34 nm restrict their use in biological applications. A wellknown approach to shifting the emission of xanthene dyes in the deep red to Near infrared (NIR) is by forming xanthene hybrids. This review gives a comprehensive list of the deep red to NIR xanthene-hemicyanine and xanthene-coumarin hybrids. We have outlined general synthetic strategies and a detailed discussion of substituent effect, π-conjugation, and ring effect on the photophysical properties of these dyes. A section on applications of deep red to NIR xanthene hybrids based on fluorophore-linker strategy and spirocyclization is included. This review highlights the structure-spectroscopic relationships, which will be useful in designing new deep red to NIR xanthene analogs.

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Section: Xanthene Dyesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

Khan

Sekar

2023

ChemistrySelect

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“…2 ). In addition, lawsones are also the essential synthons 28 for the synergistic nucleophilicity and electrophilicity to overcome various of synthetic challenges 29 – 31 . Despite being appealing structural motifs, highly efficient approaches to prepare lawsones and indenopyrazoles are limited 32 – 41 .…”

Section: Introductionmentioning

confidence: 99%

Switchable synthesis of natural-product-like lawsones and indenopyrazoles through regioselective ring-expansion of indantrione

Yan

Jiang

et al. 2023

Commun Chem

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Lawsones and indenopyrazoles are the prevalent structural motifs and building blocks in pharmaceuticals and bioactive molecules, but their synthesis has always remained challenging as no comprehensive protocol has been outlined to date. Herein, a metal-free, ring-expansion reaction of indantrione with diazomethanes, generated in situ from the N-tosylhydrazones, has been developed for the synthesis of lawsone and indenopyrazole derivatives in acetonitrile and alcohol solvents, respectively. It provides these valuable lawsone and pyrazole skeletons in good yields and high levels of diastereoselectivity from simple and readily available starting materials. DFT calculations were used to explore the mechanism in different solutions. The synthetic application example also showed the prospects of this method for the preparation of valuable compounds.

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“…Moreover, it has been used as the starting material for the synthesis of a variety of biologically active compounds and materials with interesting properties. [28][29][30][31] This review highlights the synthesis of benzo[a]phenazin-5-ol derivatives from lawsone and benzene-1,2-diamines and their applications for the construction of a variety of ve and six membered fused heterocycles.…”

Section: Introductionmentioning

confidence: 99%

A review on lawsone-based benzo[a]phenazin-5-ol: synthetic approaches and reactions

Olyaei

Sadeghpour

2022

RSC Adv.

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Recent progress on the synthesis of henna-based dibenzoxanthenes

Abstract: Xanthenes are a class of natural and synthetic heterocyclic compounds that exhibit a broad spectrum of biological properties and synthetic applications.

Cited by 10 publications

References 61 publications

Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

Switchable synthesis of natural-product-like lawsones and indenopyrazoles through regioselective ring-expansion of indantrione

A review on lawsone-based benzo[a]phenazin-5-ol: synthetic approaches and reactions

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