Intramolecular charge transfer-induced solvatochromism and large Stokes shifts of furocoumarins

Chan, Nadia Nabihah Mohd Yusof; Idris, Azila; Abidin, Zamri Zainal; Tajuddin, Hairul Anuar; Abdullah, Zanariah

doi:10.1016/j.matchemphys.2021.125406

Cited by 13 publications

(2 citation statements)

References 104 publications

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“…Original persubstituted 2-aminofurans were prepared this way, in tetrachloroethane or acetic acid, in good to excellent yields. It is worth mentioning that this synthesis allowed for the preparation of new indole-substituted furocoumarin of type 3xc whose potential photophysical, photochemical, and biological properties remain to be explored . The major limitation of this transformation resides in the use of acyclic 1,3-dicarbonyl compounds; reactions conducted with acetylacetone or ethyl acetoacetate led to complex crude mixtures.…”

Section: Resultsmentioning

confidence: 99%

Ynamides in Radical Reactions: A Route to Original Persubstituted 2-Aminofurans

et al. 2023

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Mn(OAc) 3 /Cu(OAc) 2 -mediated reaction between ynamides, derived from oxazolidone or 3-methylindole carboxylate, and cyclic α-dicarbonyl radicals led to the one-pot synthesis of 2aminofurans. The transformation involves addition of the α-dicarbonyl radical to ynamide, oxidation to ketene-iminium, and polar cyclization steps to provide original persubstituted 2-aminofurans in good to excellent yields. This work represents the first radical route for the synthesis of furans from ynamides.

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Section: Resultsmentioning

confidence: 99%

Ynamides in Radical Reactions: A Route to Original Persubstituted 2-Aminofurans

et al. 2023

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“…Fluorophores functionalized with pyridinium group(s) have attracted numerous attentions in organelle-specific imaging [52][53][54][55][56], due to the easy introduction of pyridinium units and the positive charge of pyridinium which promotes the probes to target the negatively charged organelle such as mitochondria via electrostatic interactions. Moreover, as reported, the construction of D-π-A architecture would bring about many benefits [57][58][59][60], such as strong ICT effect, large Stokes shift, which is vital to the imaging applications [61][62][63][64], long-wavelength emission, environmental sensitivity, tunable photophysical properties, and even photosensitizing properties, etc. (Scheme 1).…”

Section: Introductionmentioning

confidence: 96%

Modulating the Luminescence, Photosensitizing Properties, and Mitochondria-Targeting Ability of D-π-A-Structured Dihydrodibenzo[a,c]phenazines

Zhang,

Wang,

Zhang

et al. 2023

Molecules

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Herein, pyridinium and 4-vinylpyridinium groups are introduced into the VIE-active N,N′-disubstituted-dihydrodibenzo[a,c]phenazines (DPAC) framework to afford a series of D-π-A-structured dihydrodibenzo[a,c]phenazines in consideration of the aggregation-benefited performance of the DPAC module and the potential mitochondria-targeting capability of the resultant pyridinium-decorated DPACs (DPAC-PyPF6 and DPAC-D-PyPF6). To modulate the properties and elucidate the structure–property relationship, the corresponding pyridinyl/4-vinylpyridinyl-substituted DPACs, i.e., DPAC-Py and DPAC-D-Py, are designed and studied as controls. It is found that the strong intramolecular charge transfer (ICT) effect enables the effective separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of DPAC-PyPF6 and DPAC-D-PyPF6, which is conducive to the generation of ROS. By adjusting the electron-accepting group and the π-bridge, the excitation, absorption, luminescence, photosensitizing properties as well as the mitochondria-targeting ability can be finely tuned. Both DPAC-PyPF6 and DPAC-D-PyPF6 display large Stokes shifts (70–222 nm), solvent-dependent absorptions and emissions, aggregation-induced emission (AIE), red fluorescence in the aggregated state (λem = 600–650 nm), aggregation-promoted photosensitizing ability with the relative singlet-oxygen quantum yields higher than 1.10, and a mitochondria-targeting ability with the Pearson coefficients larger than 0.85. DPAC-D-PyPF6 shows absorption maximum at a longer wavelength, slightly redder fluorescence and better photosensitivity as compared to DPAC-PyPF6, which consequently leads to the higher photocytotoxicity under the irradiation of white light as a result of the larger π-conjugation.

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