Effect of host–guest complex formation on the fluorescence of 6-methoxy-1-methyl-quinolinium cation with 4-sulfonatocalix[4]arene: utilization as a fluorescent probe for the study of difenzoquat binding

Harangozó, József G.; Miskolczy, Zsombor; Biczók, László; Wintgens, Véronique; Lorthioir, Cédric

doi:10.1007/s10847-014-0464-9

Cited by 7 publications

(6 citation statements)

References 31 publications

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“…For example, different local dielectric environments in the host cavity can either enhance or quench fluorescence, 6,7 and the confinement of the delocalized electrons by the host cage can also dramatically modify the fluorescence of the hosted chromophore. 8 Partial shielding of the interactions with the solvent may as well play a role, e.g. by preventing photo-induced electron transfer from solvent ions.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular influence on cis–trans isomerization probed by ion mobility spectrometry

Czerwinska

Kulesza

Choi

et al. 2016

Phys. Chem. Chem. Phys.

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We used tandem ion mobility spectrometry measurements to investigate how the photo-isomerization of a chromophore (a methylpyridinium derivative) is affected by the complexation with a crown ether. A dramatic blue-shift of the photo-isomerization spectrum was observed upon complexation, which could be well reproduced by ab initio calculations. Our results support that the observed changes in the photo-physical properties of the chromophore originate from the charge-solvation of its pyridinium moiety by the host cage.

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Section: Introductionmentioning

confidence: 99%

Supramolecular influence on cis–trans isomerization probed by ion mobility spectrometry

Czerwinska

Kulesza

Choi

et al. 2016

Phys. Chem. Chem. Phys.

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“…26,27 The photophysical behavior and inclusion complex formation of 6-methoxy-1-methylquinolinium (C 1 C 1 OQ + ) were investigated, 28 and the substantial change of its fluorescence was used to detect the embedment of a herbicide in 4-sulfonatocalix [4]arene (SCX4). 29 For the rational design of tailor-made self-assembled systems incorporating SCXn hosts, the deeper understanding of the relationship between the molecular structure of the components and the driving force of encapsulation is of crucial importance. In the present study, we reveal how the systematic variation of the length and the location of the alkyl chain in quinolinium derivatives influence the thermodynamics of binding and the structure of the produced inclusion complex.…”

Section: Introductionmentioning

confidence: 73%

“…6-Methoxyquinolinium derivatives are important fluorophores because they can be used in aqueous solution in a wide pH range and emit substantially Stokes-shifted strong fluorescence. Members of this class of compounds were applied as probes for the detection of the intracellular Cl – levels − and the monitoring of Cl – transport across cell membranes. , The photophysical behavior and inclusion complex formation of 6-methoxy-1-methylquinolinium (C 1 C 1 OQ + ) were investigated, and the substantial change of its fluorescence was used to detect the embedment of a herbicide in 4-sulfonatocalix[4]arene (SCX4) …”

Section: Introductionmentioning

confidence: 76%

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Substituent Effects on the Inclusion of 1-Alkyl-6-alkoxy-quinolinium in 4-Sulfonatocalix[n]arenes

et al. 2018

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The effect of the chain length of the alkyl and alkoxy substituents on the binding characteristics of 1-alkyl-6-alkoxy-quinolinium cations was studied using 4-sulfonatocalix[4]arene (SCX4) and 4-sulfonatocalix[6]arene (SCX6) in neutral aqueous solutions at 298 K. Isothermal calorimetric titrations showed enthalpy-controlled inclusion with 1:1 stoichiometry. The equilibrium constants of complexation were always larger for the confinement in SCX4 than in its SCX6 homologue because the better matching between the host and guest sizes allowed more exothermic interaction. The binding affinity diminished with the lengthening of the aliphatic chain of the guests in the case of the association with SCX4, but insignificant change was found for SCX6 complexes. The most substantial change in the enthalpic and entropic contributions to the driving force of complex production occurred when the alkyl chain was linked to the heterocyclic nitrogen and the number of its carbon atoms varied between 1 and 4. 1 H NMR spectra evidenced that in SCX6, the 1-alkyl-6-alkoxy-quinolinium cations could be included within the macrocycle cavity. In the case of SCX4, the quinolinium ring is always inside the host, but the alkyl chain is included within SCX4 only for a short chain length ( n up to 4). In contrast, the alkoxy chain displays a very weak interaction with the cavity irrespective of the length. Because of the outward orientation from the host, the lengthening of the alkoxy substituent of the quinolinium moiety barely influenced the thermodynamics of inclusion in SCX4. Distinct linear enthalpy–entropy correlations were found for the encapsulation in SCX4 and SCX6.

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“…Protonation and/or deprotonation of the amine bridge of luminescence of [Ru(bpy)2(phen‐CD)] 2+ enhanced its sensitivity toward pH and displacement of the dyad from the cavity 6A‐(5‐amino‐1, 10‐phenanthroline)‐6A‐deoxy‐β‐CD by anthraquinone and anthraquinone‐2‐carboxylic acid quencher enhances PET between an included guest and the ruthenium center via MLCT mechanism (47). In another research, displacement of 6‐methoxy‐1‐methyl‐quinolinium C1MQ from the cavity of 4‐sulfonatocalix[4]arene (SCX4) by difenzoqua herbicide (DFQ) quenched the fluorescence of C1MQ and resulted in the difference in fluorescence quantum yields of free and bound C1MQ (48), while Calixarenes as an electron donor was also utilized to build a well‐assembled nanomaterial capable transferring electron and energy within a framework (49).…”

Section: Mechanisms To Enhance Pet Quenching By a Supramolecular Appr...mentioning

confidence: 99%

Photoinduced Electron Transfer in Encapsulated Heterocycles by Cavitands

Bojesomo

Saleh

2021

Photochem & Photobiology

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Host−guest complexation of small heterocyclic (guest) and macrocyclic cavitands (hosts) organic molecules is still to date a very popular, inexpensive approach that bypasses the burdens of conventional covalent synthesis. Understanding the selection criteria of these chemicals is crucial to the design and potential applications of their supramolecular assemblies. This review surveys examples within the last 15 years (2005–2020) of supramolecular complexes in which the interacting photoinduced electron transfer (PET)‐based chromophore and quencher fragments are commonly used in the market with reported CAS numbers. It appears from this survey that the supramolecular effects can be directed to specifically disrupt PET when the nonemissive macrocycles separately encapsulate the fluorescent acceptor or donor molecules, among other specific factors, such as when inducing conformational changes or pKa shift of the donor. On the contrary, synergetic encapsulation of both donor and acceptor molecules, formation of ternary self‐assembly at the rim or encapsulation of one component while grafting the other onto the macrocycle, among other specific factors such as the modulation of the excited‐state structure of donor, will lead to the enhancement of PET process. In the event the donor or acceptor molecules have multitopic structures, the PET process can repeatedly be switched on and off. It is generally concluded that understanding the criteria for the combination of these available products for the purpose of manipulating their PET efficiency should pave the way for the facile alternative generation of new noncovalently bonded host−guest supramolecular assemblies with a more specific design tailored for more advanced, diverse and economic applications such as chemical sensing, molecular gates, drug delivery and biolabeling.

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Effect of host–guest complex formation on the fluorescence of 6-methoxy-1-methyl-quinolinium cation with 4-sulfonatocalix[4]arene: utilization as a fluorescent probe for the study of difenzoquat binding

Cited by 7 publications

References 31 publications

Supramolecular influence on cis–trans isomerization probed by ion mobility spectrometry

Supramolecular influence on cis–trans isomerization probed by ion mobility spectrometry

Substituent Effects on the Inclusion of 1-Alkyl-6-alkoxy-quinolinium in 4-Sulfonatocalix[n]arenes

Photoinduced Electron Transfer in Encapsulated Heterocycles by Cavitands

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