Self-healing, luminescent metallogelation driven by synergistic metallophilic and fluorine–fluorine interactions

Kolari, Kalle; Bulatov, Evgeny; Tatikonda, Rajendhraprasad; Bertula, Kia; Kalenius, Elina; Nonappa, Nonappa; Haukka, Matti

doi:10.1039/c9sm02186h

Cited by 8 publications

(4 citation statements)

References 65 publications

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“…The microscopic changes occurring in molecular gels are attributed to noncovalent intermolecular interactions responsible for the molecular self-assembly. The noncovalent interactions such as hydrogen bonding, electrostatic effect, hydrophobic effect, London dispersion forces, van der Waals interactions, charge-transfer complexation, metal coordination, − halogen bonding, and fluorine–fluorine interactions , have been explored effectively for designing new gelators. Extensive research, pursued over the last three decades on diverse building blocks, has offered the possibilities toward the rational design of molecular gelators with unique material properties.…”

Section: Introductionmentioning

confidence: 99%

Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates

et al. 2021

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Natural and abundant plant triterpenoids are attractive starting materials for the synthesis of conformationally rigid and chiral building blocks for functional soft materials. Here, we report the rational design of three oleanolic acid–triazole–spermine conjugates, containing either one or two spermine units in the target molecules, using the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The resulting amphiphile-like molecules 2 and 3, bearing just one spermine unit in the respective molecules, self-assemble into highly entangled fibrous networks leading to gelation at a concentration as low as 0.5% in alcoholic solvents. Using step-strain rheological measurements, we show rapid self-recovery (up to 96% of the initial storage modulus) and sol ⇔ gel transition under several cycles. Interestingly, rheological flow curves reveal the thixotropic behavior of the gels. To the best of our knowledge, this kind of behavior was not shown in the literature before, neither for a triterpenoid nor for its derivatives. Conjugate 4, having a bolaamphiphile-like structure, was found to be a nongelator. Our results indicate that the position and number of spermine units alter the gelation properties, gel strength, and their self-assembly behavior. Preliminary cytotoxicity studies of the target compounds 2–4 in four human cancer cell lines suggest that the position and number of spermine units affect the biological activity. Our results also encourage exploring other triterpenoids and their derivatives as sustainable, renewable, and biologically active building blocks for multifunctional soft organic nanomaterials.

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Section: Introductionmentioning

confidence: 99%

Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates

et al. 2021

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“…[18][19][20][21][22][23][24][25][26][27] In addition, unique polymorphism originated from noncovalent interactions such as metal-ligand, metal-metal, and π-electron interaction enables Pt(II)-tpy to construct a variety of intriguing self-assembled nanostructures. [28][29][30][31][32][33][34][35] In this research, a Pt(II)-tpy-based new metallomesogen was synthesized for the development of a novel luminescent material exhibiting thermo-responsive and linearly polarized light emission. Furthermore, the correlation between the self-assembled structure and the luminescence characteristics was thoroughly investigated based on thermodynamics and kinetics to control the extraordinary optoelectronic and photophysical properties of the metallomesogen-based hierarchical nanostructures.…”

Section: Introductionmentioning

confidence: 99%

Cyclometalated Pt(II)‐Terpyridine Metallomesogen: What Is Visible or Invisible That Is a Matter of Molecular Packing and Orientation

Kang

Rim

Ryu

et al. 2021

Adv Funct Materials

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An anisotropic light emitting metallomesogen (PtM) consisting of a cyclometalated platinum(II)-terpyridine (Pt(II)-tpy) chromophore and a flexible dendron is newly synthesized as a thermal-induced and polarization-induced solid-state luminescence switching material. The self-assembled PtM is uniaxially aligned by mechanical shearing within the mesophase resulting in high optical anisotropy with chromophores. The shear-induced metastable PtM crystal exhibits emission change depending on the polarization direction and thermally triggered reversible emission quenching-recovery characteristic. In order to precisely control the optical feature of the PtM, the self-assembled supramolecular structure and thermal-sensitive photophysical properties are characterized. Based on the multiresponsive luminescence switching system of PtM, a multiplexed optical code is encrypted with a simple coating and its feasibility for optical anticounterfeiting applications is demonstrated.

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“…5,6 Among them, terpyridine-platinum complexes hold significant promise because of their unique structural and functional properties. [7][8][9][10] In this context, square-planar platinum(II) d 8 complexes represent attractive building blocks for supramolecular architectures, which possess intriguing spectroscopic and luminescence properties. [11][12][13][14][15][16] They show a strong propensity to self-assemble into highly ordered supramolecular polymers via noncovalent interactions, such as hydrogen bonding, metal-metal, and p-p interactions.…”

mentioning

confidence: 99%

“…5,6 Among them, terpyridine–platinum complexes hold significant promise because of their unique structural and functional properties. 7–10…”

mentioning

confidence: 99%

Platinum(ii) terpyridine-based supramolecular polymer gels with induced chirality

Kang,

Lee,

Seo

et al. 2023

Soft Matter

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Self-healing, luminescent metallogelation driven by synergistic metallophilic and fluorine–fluorine interactions

Abstract: Aggregation and self-assembly of terpyridine platinum(ii) complex with fluorinated alkyl substituent, driven by synergistic metallophilic and fluorophilic interactions, result in formation of a robust, self-healing, and luminescent gel.

Cited by 8 publications

References 65 publications

Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates

Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates

Cyclometalated Pt(II)‐Terpyridine Metallomesogen: What Is Visible or Invisible That Is a Matter of Molecular Packing and Orientation

Platinum(ii) terpyridine-based supramolecular polymer gels with induced chirality

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