Novel long alkyl side chain benzo[a]phenoxazinium chlorides: synthesis, photophysical behaviour and DNA interaction

Alves, Carla; Naik, Sarala; Coutinho, Paulo J. G.; Gonçalves, M. Sameiro T.

doi:10.1016/j.tet.2009.10.017

Cited by 34 publications

(45 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…14, 4 15 In ethanol media the absorption spectra are dominated by an acidic form (AH + ) and a 100 nm blue shifted neutral form (A). 16 The fluorescence of the basic form is broad and centred at around 600 nm while the acid form (AH + ) shows a band centred above 660 nm with a much higher quantum yield.…”

Section: Resultsmentioning

confidence: 99%

Benzo[a]phenoxazinium chlorides functionalized with chloride atoms and/or ester groups

Leitão¹,

Raju²,

Sousa³

et al. 2015

Proceedings of the 19th International Electronic Conference on Synthetic Organic Chemistry

Self Cite

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Benzo[a]phenoxazinium chlorides functionalized with chloride atoms and/or ester groups

Leitão¹,

Raju²,

Sousa³

et al. 2015

Proceedings of the 19th International Electronic Conference on Synthetic Organic Chemistry

Self Cite

View full text Add to dashboard Cite

“…9,10 In ethanol media the absorption spectra are dominated by an acidic form (AH + ) and a ~100nm blue shifted neutral form (A).…”

Section: Resultsmentioning

confidence: 99%

“…Through the stiffening of 9-amino position, it was expected that the fluorescence quantum yield in acidified ethanol should be higher than the values previously obtained for benzophenoxazines without a fused julolidine moiety and di-alkylated compounds (between 0.1 and 0.2). 9,10,12 In fact, the improvement in fluorescence quantum yield was not observed which can be explained by the possible presence of aggregates in ethanolic media that was evidenced in the broader spectrum of the studied compounds in acidified ethanol. Nevertheless, it seems that the 5-amino position (6-or 14-positions in 1 and 2a-d, respectively) is the main pathway of excited state nonradiative desactivation.…”

mentioning

confidence: 93%

“…3 Moreover, they are useful as photosensitizers in photodynamic therapy, fluorophor in energy and electron-transfer reactions antitubercolastatic or anticancerogenic agents. 4 In the previous reports by our research group we have synthesised several NB derivatives, [5][6][7][8][9][10] and in the present communication we are interested to explore the properties of a rigid structure in comparison with the unrestricted dye. Herein, we report the synthesis of benzophenoxazinium derivaties fused with julolidine moiety.…”

Section: Introductionmentioning

confidence: 99%

“…12 The later reaches 0.4 when the 9-amino position is mono-alkylated and varies between 0.1 and 0.2 when it is dialkylated. 9,10,12 At 470nm the basic form is mostly excited with a small fraction of acidic form. At higher wavelengths the situation is reversed.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Photophysics of New Benzophenoxazine Derivatives Fused with Julolidine

Raju

Ribeiro

Coutinho

et al. 2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

show abstract

In Situ Synthesis of Phenoxazine Dyes in Water: Application for “Turn‐On” Fluorogenic and Chromogenic Detection of Nitric Oxide**

et al. 2022

View full text Add to dashboard Cite

The synthesis of phenoxazine dyes was revisited in order to access these fluorescent N,O-heterocycles under mild conditions. The combined sequential use of nitrosonium tetrafluoroborate (NOBF 4 ) and triphenylphosphine enables the facile conversion of bis(3-dimethylaminophenyl) ether into the methyl analogue of popular laser dye oxazine 1. The ability of nitrosonium cation (NO + ) to initiate the domino reaction resulting in π-conjugated phenoxazine molecules under neutral conditions, then led us to explore the feasibility of expanding it in aqueous media. Thus, we explored the use of reactive signaling molecule nitric oxide (NO) as a biological trigger of phenoxazine synthesis in water. The implementation of a robust analytical methodology based on fluorescence assays and HPLC-fluorescence/-MS analyses, have enabled us to demonstrate the viability of this novel fluorogenic reaction-based process to selectively yield an intense "OFF-ON" response in the near-infrared (NIR-I) spectral region. This study is an important step towards the popularization of the concept of "covalent assembly" in the fields of optical sensing, bioimaging and molecular theranostics.

show abstract

Novel long alkyl side chain benzo[a]phenoxazinium chlorides: synthesis, photophysical behaviour and DNA interaction

Cited by 34 publications

References 24 publications

<strong>Benzo[</strong><em><strong>a</strong></em><strong>]phenoxazinium chlorides functionalized with chloride atoms and/or ester groups</strong>

<strong>Benzo[</strong><em><strong>a</strong></em><strong>]phenoxazinium chlorides functionalized with chloride atoms and/or ester groups</strong>

Synthesis and Photophysics of New Benzophenoxazine Derivatives Fused with Julolidine

In Situ Synthesis of Phenoxazine Dyes in Water: Application for “Turn‐On” Fluorogenic and Chromogenic Detection of Nitric Oxide**

Contact Info

Product

Resources

About