Calixarenes and Fullerenes

Georghiou, Paris E.

doi:10.1007/978-3-319-31867-7_33

Cited by 18 publications

(14 citation statements)

References 76 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the field of supramolecular chemistry, host–guest association through noncovalent interactions is an interesting and exciting topic, especially for the encapsulation of various fullerenes, such as C 60 and C 70 [ 1 – 5 ]. It is generally accepted that good complexation of fullerenes requires host molecules with bowl or basket-like shapes, such as calixarenes [ 6 ], corannulenes [ 7 – 10 ], cyclodextrins [ 11 – 13 ], cyclotriveratrylenes [ 14 – 16 ], and similar macrocycles [ 17 – 20 ]. Tribenzotriquinacene (TBTQ) and its derivatives, owing to their unique rigid, C 3 v -symmetric, concave-convex trifuso-triindane skeleton that consists of three perfectly orthogonally oriented indane wings, bear a similar potential as molecular hosts.…”

Section: Introductionmentioning

confidence: 99%

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

Liu¹,

Wang²,

Li³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A sugar-functionalized water-soluble tribenzotriquinacene derivative bearing six glucose residues, TBTQ-(OG) 6 , was synthesized and its interaction with C60 and C70-fullerene in co-organic solvents and aqueous solution was investigated by fluorescence spectroscopy and ultraviolet-visible spectroscopy. The association stoichiometry of the complexes TBTQ-(OG) 6 with C60 and TBTQ-(OG) 6 with C70 was found to be 1:1 with binding constants of K a = (1.50 ± 0.10) × 105 M−1 and K a = (2.20 ± 0.16) × 105 M−1, respectively. The binding affinity between TBTQ-(OG) 6 and C60 was further verified by Raman spectroscopy. The geometry of the complex of TBTQ-(OG) 6 with C60 deduced from DFT calculations indicates that the driving force of the complexation is mainly due to the hydrophobic effect and to host–guest π–π interactions. Hydrophobic surface simulations showed that TBTQ-(OG) 6 and C60 forms an amphiphilic supramolecular host–guest complex, which further assembles to microspheres with diameters of 0.3–3.5 μm, as determined by scanning electron microscopy.

show abstract

Section: Introductionmentioning

confidence: 99%

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

Liu¹,

Wang²,

Li³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Since calixarenes have a cavity composed of aromatic rings and fullerenes are covered by π-electrons, selfassembly through strong π-π interactions may occur between each other [12]. The good compatibility between spherical (C60) or ellipsoid (C70) fullerenes and ball-shaped cavity of calixarenes to form complexes both in solution and in the solid state, have been extensively investigated [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…Calixarene-fullerene complexation studies in solution usually rely on NMR and/or UV-Vis measurements [15][16][17], although fluorescence spectroscopy also been used [14,18].…”

Section: Introductionmentioning

confidence: 99%

A New Fluorescent Calixarene Dimer: Synthesis, Optical Properties, and Sensory Applications

Costa

Barata

Costa

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

A new fluorogenic bis-calix[4]arene-carbazole compound (3) with an enlarged intramolecular cavity able to be involved in host:guest chemistry with large organic guests was designed. Its synthesis was accomplished for the first time using a Sonogashira-Hagihara crosscoupling reaction in the final step. The calixarene receptor was structurally characterized by FTIR and 1 H/ 13 C/2D NMR techniques and its photophysical properties evaluated. The ability of 3 to form supramolecular complexes with fullerenes (C60 and C70) was evaluated through fluorimetric titration experiments. The value of the binding constants (K3:C60 = 1.39x10 5 M −1 and K3:C70= 6.88x10 4 M −1), and the free energy changes for the inclusion complexation (G3:C60 = −29.33 kJ/mol and G3:C70 = −27.60 kJ/mol), revealed a high sensitivity of the calixarene-carbazole host for both fullerenes. The host molecule shown to be particularly selective towards fullerene C60.

show abstract

“…This all-hydrocarbon, wide-rim octaphenyl-functionalized calix[4]azulene was designed to evaluate its potential for encapsulating C 60 or C 70 fullerenes. The lack of sufficient solubility of 5 in common organic solvents prevented a fuller examination of its potential supramolecular properties with fullerenes, a topic of particular interest to us [ 18 ]. Therefore, the solid state supramolecular complexation properties of 5 were experimentally studied using solid state NMR and XRD experiments, and also theoretically, using a DFT analysis [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Calixazulenes: azulene-based calixarene analogues – an overview and recent supramolecular complexation studies

Georghiou¹,

Rahman²,

Alodhayb³

et al. 2018

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Some of the least studied calixarenes are those that consist of azulene rings bridged by -CH2- groups. Since Lash and Colby’s discovery of a simple and convenient method for producing the parent all-hydrocarbon calix[4]azulene, there have been two other all-hydrocarbon calix[4]azulenes which have been synthesized in good yields by their method. This allowed studying their supramolecular properties. This report is of our latest work on the solution-state supramolecular complexation of one of these calix[4]azulenes, namely tetrakis(5,7-diphenyl)calix[4]azulene or “OPC4A”, with several electron-deficient tetraalkyammonium salts. As a result of more recent methods developed by us and others employing Suzuki–Miyaura cross-coupling reactions to produce additional functionalized azulenes, the promise of further greater functionalized calixazulenes lies in store to be investigated.

show abstract

Calixarenes and Fullerenes

Cited by 18 publications

References 76 publications

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

A New Fluorescent Calixarene Dimer: Synthesis, Optical Properties, and Sensory Applications

Calixazulenes: azulene-based calixarene analogues – an overview and recent supramolecular complexation studies

Contact Info

Product

Resources

About