Synthesis and photophysical characterization of heterocyclic dihydrotetracenes and their utility in the fluorescence imaging of HeLa cells

Banerjee, Subhadeep; Phadte, Apeksha Ashok; Chattopadhyay, Asis Kumar; Fernandes, Joseph R.D.; Savardekar, Akanksha Vinod; Banerjee, Arundhati

doi:10.1016/j.tetlet.2018.09.013

Cited by 7 publications

(30 citation statements)

References 27 publications

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“…The compounds 7 a‐c exhibited typical 2‐band dibenzodioxin spectrum with the strongest band at about 260 nm and a weaker broad peak centered on 377 nm ( 7 a ), 396 nm ( 7 b ) and 373 nm ( 7 c ) (SI, Table S1), in similar ranges to earlier observed dibenzodioxins . …”

Section: Resultssupporting

confidence: 74%

“…Since we learned that 1 b , 1 c and 2 b , 2 c exhibited moderate emission strength despite possessing the carboxy methyl ester group, we were interested to design and prepare more such analogs with different electron withdrawing groups. To this end, new dibenzodioxin compounds 7 a – c (Scheme ) were prepared from suitably substituted catechols 6 a‐c and fluorinated nitrile 5 using our simple and high yielding method of dibenzodioxin synthesis .…”

Section: Resultsmentioning

confidence: 99%

“…When the F atoms in 1 a‐c were replaced by electron donating nucleophiles like Et 2 NH, ethylene diamine and ethanolamine, newer fluorescent derivatives ( 2 a‐c , 3 and 4 ) could be developed which had strong absorption peaks in the range of ∼400‐472 nm and emission peaks as far out as 525 nm . In fact compound 2 a exhibited strongest emission efficiency among all dibenzodioxins prepared thus far and proved its utility in microscopic imaging of HeLa cells .…”

Section: Introductionmentioning

confidence: 99%

“…In course of our research into design and synthesis of novel fluorescent organic molecules, we have developed several push‐pull type dibenzodioxins and phenazines, some of which have shown moderate to good emission capacity, while some others are non‐emissive . These molecules have proven their potential in (1) medicinal chemistry as anti‐tumor agents in vitro ,, (2) as fluorescent imaging agents in microscopy and as (3) pH sensitive probes . These functions were attributed to the extensive charge delocalization possible in the molecules, through the push and pull groups connected by an anthracene‐like heteroaromatic (dibenzodioxin/phenazine) moiety.…”

Section: Introductionmentioning

confidence: 99%

“…Interestingly, the presence of an additional electron withdrawing group did not reduce their fluorescence efficiency compared to 1 a . Theoretical calculations showed that the charge transfer from dioxin ring to the benzonitrile moiety was not significantly affected despite presence of an extra electron withdrawing group; only modest (∼5‐6 nm) blue shifts were observed in their UV‐visible spectrum …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Green Emitting Multi‐substituted Dibenzodioxins and Related Heteroacenes and Computational Investigation of Substituent Effects on Emission Spectra

et al. 2020

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Push‐pull dibenzodioxins with electron withdrawing and donating groups were prepared in good yields through a short and simple synthesis. Strong green emission above 500 nm occurs in those derivatives where there is maximum charge transfer to the most electron deficit terephthalonitrile ring, from proximal cyclic amino donor groups. Theoretical calculations support experimental findings through evaluation of excited state properties. In molecules with a nitro group, the excited state localizes electron density exclusively onto it and twisted nitro geometry was also found. In effect, electronic charge cannot relocate into the molecular plane, rendering them non‐fluorescent. Also, studies on the fluorescent derivatives show that best emission would occur when the donor moiety contains a saturated cyclic amino ring and the amines are 2°. Overall, our study establishes structure‐property guidelines and limits on dibenzodioxin functionalization towards preparing fluorescent derivatives of the same.

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Section: Resultssupporting

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Green Emitting Multi‐substituted Dibenzodioxins and Related Heteroacenes and Computational Investigation of Substituent Effects on Emission Spectra

et al. 2020

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Amino‐Terephthalonitrile and Amino‐Terephthalate‐Based Single Benzene Fluorophores – Compact Color Tunable Molecular Dyes for Bioimaging and Bioanalysis

Raghava,

Banerjee

2024

Chemistry An Asian Journal

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This review article discusses the emerging amino‐terephthalonitrile (Am‐TN) and amino terephthalate‐based single benzene fluorophores (SBFs) for their highly emissive nature and potential for numerous technical applications. Am‐TN‐SBFs are a new class of SBFs having amine as the electron donating (EDG) and dinitrile as the electron withdrawing group (EWG). The beauty of these Am‐TN‐SBFs lies in excellent intramolecular charge transfer between the EDG and EWG. The placement of two nitrile groups in para‐position on the benzene ring allows better charge transfer from the donating amines to the linear nitrile group leading to the strongly emissive nature. We also outline here the latest developments in the well‐known family of amino terephthalate SBFs reported in the last 2 to 3 years. Amino terephthalate SBFs have esters as the EWG and amine as the EDG. These have intramolecular H‐bonding between the EDG and EWG which is responsible for their emissive behavior.

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An Electrochemical Investigation into the Redox Properties of Push‐Pull Dibenzodioxins and Comparative Analysis with Analogous Heteroacenes

2022

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A series of dibenzodioxins containing electron push-pull groups were synthesized using simple methods and their spectroscopic and redox behavior was studied. Electrochemical experiments were performed to measure the redox potentials of the substituted dibenzodioxins. The role of individual molecular subunits in tweaking the redox potential values was delineated by comparing them with the electrochemical properties of analogous heteroacenes. In many cases, our redox potentials were found to be comparably low with that of many wellknown heteroacenes.

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Synthesis and photophysical characterization of heterocyclic dihydrotetracenes and their utility in the fluorescence imaging of HeLa cells

Cited by 7 publications

References 27 publications

Synthesis of Green Emitting Multi‐substituted Dibenzodioxins and Related Heteroacenes and Computational Investigation of Substituent Effects on Emission Spectra

Synthesis of Green Emitting Multi‐substituted Dibenzodioxins and Related Heteroacenes and Computational Investigation of Substituent Effects on Emission Spectra

Amino‐Terephthalonitrile and Amino‐Terephthalate‐Based Single Benzene Fluorophores – Compact Color Tunable Molecular Dyes for Bioimaging and Bioanalysis

An Electrochemical Investigation into the Redox Properties of Push‐Pull Dibenzodioxins and Comparative Analysis with Analogous Heteroacenes

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