Encapsulation of rhodamine-6G within p-sulfonatocalix[n]arenes: NMR, photophysical behaviour and biological activities

Patil, Sanhita; Athare, Sulakshana V.; Jagtap, Ashok S.; Kodam, Kisan M.; Gejji, Shridhar P.; Malkhede, Dipalee D.

doi:10.1039/c6ra23614f

Cited by 20 publications

(13 citation statements)

References 51 publications

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“…Host-guest species were generated using Autodock Vina [41] (See experimental section for more details), the lowest energy conformer (Figure 8) involves the pendant benzoate moiety of the R6G bound within the SO 2 C [4] cavity via π-π interactions, in line with previous studies, [33] and is also borne out for the other five lowest energy conformations (Figure S13). The SO 2 C[4]�R6G complex is augmented by weak CH-hydrogen bonds between the R6G arylmethyl groups to the calixarene sulfonate (SOÀ HC mean = 3.5 Å), with an overall distance between the R6G centroid and the Tb ion of 9.4 Å (Figure S14 for centroid definition) and a net stabilization of À 16 kJ.mol À 1 upon formation of the host-guest species.…”

Section: Based On τ D Based On I Dmentioning

confidence: 84%

“…A particular feature is that both absorption and emission spectra overlap the emission spectrum of Tb (Figure 4). Noteworthy, evidence of R6G interaction with p-sulfonatocalixarenes and p-sulfonato-thiacalixarenes have already been reported in the literature, [33,34] and its inclusion via encapsulation of the benzoate moiety of the R6G guest within the calixarene cavity was investigated. [33] However, to the best of our knowledge, no study on the interaction between R6G and p-sulfonato-sulfoxocalix [4]arene, SO 2 C [4], has been reported up to date.…”

Section: Interaction Of Rhodamine 6g With So 2 C[4]) Capped Tbnpsmentioning

confidence: 97%

“…Noteworthy, evidence of R6G interaction with p-sulfonatocalixarenes and p-sulfonato-thiacalixarenes have already been reported in the literature, [33,34] and its inclusion via encapsulation of the benzoate moiety of the R6G guest within the calixarene cavity was investigated. [33] However, to the best of our knowledge, no study on the interaction between R6G and p-sulfonato-sulfoxocalix [4]arene, SO 2 C [4], has been reported up to date. We thus aimed to investigate the possible interaction of R6G with SO 2 C [4] capped at the surface of the NPs.…”

Section: Interaction Of Rhodamine 6g With So 2 C[4]) Capped Tbnpsmentioning

confidence: 97%

“…From the fitting of the data of Figure 5, a very strong association constant of 2.5(8) × 10 7 M À 1 was calculated. Noteworthy, the inclusion of R6G into C [4] and SC [4] (not bound to a NP) has already been studied in d 6 -DMSO solutions by 1 H NMR spectroscopy, [33] but the reported values of the association constants are far smaller in that case, 2.5 and 1.32 M À 1 , respectively. Unfortunately, the very low solubility of R6G in D 2 O precluded the study of the inclusion monitored by 1 H NMR.…”

Section: Interaction Of Rhodamine 6g With So 2 C[4]) Capped Tbnpsmentioning

confidence: 99%

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Investigation of the Supramolecular Assembly of Luminescent Lanthanide Nanoparticles Surface Functionalized by p‐Sulfonato‐Calix[4]arenes with Charged Aromatic Compounds

et al. 2021

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The surface coordination of p-sulfonato- (C[4]), p-sulfonatothia- (SC[4]) and p-sulfonato-sulfoxocalix [4]arene (SO 2 C[4]) on La 0.9 Tb 0.1 F 3 nanoparticles (TbNP) was investigated by UV-Vis absorption and luminescence spectroscopies. SO 2 C[4] displayed the strongest affinity towards the NPs and a significant antenna effect leading to observation of the characteristic Tb emission bands upon calixarene excitation. NPs decorated by a shell of SO 2 C[4] were prepared and the interaction with rhodamine 6G (R6G) was studied. The progressive addition of R6G resulted in a strong Tb to R6G energy transfer process, as revealed by a long lived emission of R6G upon SO 2 C[4] excitation. The FRET efficiency was almost quantitative (87-90 %), pointing to an average distance of 28 to 32 Å between the R6G and the Tb emitting centres of the NP. An association of one R6G per SO 2 C[4] was deduced with a very strong apparent affinity (K = 2.5 × 10 7 M À 1 ) in water. Similar interactions were observed with paraquat, resulting in TbNP luminescence quenching. In both cases, an unexpected increase of the association constant of the cation with SO 2 C[4] was observed when SO 2 C[4] is anchored at the surface of the NP.

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Section: Based On τ D Based On I Dmentioning

confidence: 84%

Section: Interaction Of Rhodamine 6g With So 2 C[4]) Capped Tbnpsmentioning

confidence: 97%

Section: Interaction Of Rhodamine 6g With So 2 C[4]) Capped Tbnpsmentioning

confidence: 97%

Section: Interaction Of Rhodamine 6g With So 2 C[4]) Capped Tbnpsmentioning

confidence: 99%

See 2 more Smart Citations

Investigation of the Supramolecular Assembly of Luminescent Lanthanide Nanoparticles Surface Functionalized by p‐Sulfonato‐Calix[4]arenes with Charged Aromatic Compounds

et al. 2021

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“…This value is marginally different from the one measured from the encapsulation kinetics. The proton resonance signals from Rh6G were assigned based on the literature data 40 . Other dye@In-BTBs were also digested in DCl and DMSO- d 6 (3:7 v/v%) for 1 H-NMR spectroscopy measurements (Table S2 ).…”

Section: Resultsmentioning

confidence: 99%

Photophysical properties of cationic dyes captured in the mesoscale channels of micron-sized metal-organic framework crystals

Choi

Yoon

Huh

et al. 2018

Sci Rep

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The optical properties of dye molecules in confined spaces can differ from the solution phase due to confinement effects. Pre-organized mesoscale channels of metal-organic frameworks (MOFs) are very suited for hosting various dyes, and the robust frameworks often render the encapsulated dyes with certain preferential geometries, which are different from those found in solution. Furthermore, pre-organized open channels can efficiently guide the uniform and unique spatial distribution of dye molecules in a controlled manner, which are otherwise difficult to achieve. Thus, sufficiently large dye molecules can avoid the formation of complex aggregates when captured inside open channels. In contrast, small dye molecules can form well-defined dimers or aggregates. The resulting dye-encapsulated MOFs can display unusual photophysical properties of the captured dyes. An anionic framework of In-BTB with mesoscale 3D channels is utilized for the efficient encapsulation of various cationic dyes through cation-exchange processes. Six different cationic dyes are encapsulated in the anionic framework of In-BTB, and their crystal structures are completely solved. Novel photophysical properties of these spatially distributed dye molecules in dye@In-BTBs are investigated.

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Exceeding 100 µs Charge Carrier Separation in Perovskite Mediated by Rhodamine 6G

Naphade

Gutiérrez‐Arzaluz

Nematulloev

et al. 2023

Advanced Optical Materials

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Halide perovskite colloidal nanocrystals (NCs) have enabled considerable progress in light conversion applications. However, the presence of unavoidable defect states and phase transition effects can accelerate undesirable rapid charge recombination of the photogenerated charge carriers. To address this issue, chromophores with an anchoring moiety are often used to modify the surface of the NCs, promoting prolonged charge separation through electron or energy transfer processes for optoelectronic applications. Here, steady‐state and time‐resolved spectroscopy methods are combined with density functional theory (DFT) calculations to explore and decipher the excited‐state interaction in colloidal CsPbX3 (X = Br, I) NCs with a rhodamine 6G (Rh6G) hybrid assembly. The results show that Rh6G dimerizes even at low concentrations, as evidenced by DFT calculations. The binding of Rh6G on the NC surface is confirmed by FTIR and NMR spectroscopy techniques. In addition, transient absorption spectroscopy reveals directional sub‐ps electron transfer from Rh6G to CsPbI3 NCs, whereas energy transfer occurs from CsPbBr3 to Rh6G, which ultimately recombines in the µs time regime. The findings highlight the simplest and most practical approaches for studying and tailoring the excited‐state interaction in colloidal perovskite NCs and chromophore assembly.

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Encapsulation of rhodamine-6G within p-sulfonatocalix[n]arenes: NMR, photophysical behaviour and biological activities

Abstract: Partial inclusion of rhodamine-6G within sulfonatocalixarene macrocycles engenders fluorescence quenching and demonstrates remarkable antiproliferative activities.

Cited by 20 publications

References 51 publications

Investigation of the Supramolecular Assembly of Luminescent Lanthanide Nanoparticles Surface Functionalized by p‐Sulfonato‐Calix[4]arenes with Charged Aromatic Compounds

Investigation of the Supramolecular Assembly of Luminescent Lanthanide Nanoparticles Surface Functionalized by p‐Sulfonato‐Calix[4]arenes with Charged Aromatic Compounds

Photophysical properties of cationic dyes captured in the mesoscale channels of micron-sized metal-organic framework crystals

Exceeding 100 µs Charge Carrier Separation in Perovskite Mediated by Rhodamine 6G

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