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Interfacial Characterization of Ruthenium-Based Amphiphilic Photosensitizers.

ABSTRACT: Nonreactive surfactant molecules have long been used and characterized for a wide range of applications in industries, life science, and everyday life. Recently, new types of functional amphiphilic molecules have emerged that bear another function, for example, a light-absorbing action, or catalytic properties. However, the surfactant properties of these molecules remain to date essentially unknown. In this context, we investigated here the interfacial activity of photocatalytic surfactants based on a ruthenium(II) tris-bipyridine core, functionalized with two alkyl tails. We realized a systematic characterization of the surfactant properties of these molecules at a water-air interface and studied the effect of the alkyl chain length and of the counterions (hexafluorophosphate or chloride) on these properties. Our data demonstrate that ruthenium surfactants with chloride counteranions form a denser layer at the interface, but their surfactant properties can dramatically deteriorate when the chain length of the alkyl tail increases, leading to simple hydrophobic molecules with poor surfactant properties for the longest chains (C17). These findings pave the way for a better use and understanding of photocatalytic soft interfaces.

SUBMITTER: Timounay Y

PROVIDER: S-EPMC9367009 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Interfacial Characterization of Ruthenium-Based Amphiphilic Photosensitizers.

Timounay Yousra Y Pannwitz Andrea A Klein David M DM Biance Anne-Laure AL Hoefnagel Marlene E ME Sen Indraneel I Cagna Alain A Le Merrer Marie M Bonnet Sylvestre S

Langmuir : the ACS journal of surfaces and colloids 20220729 31

Nonreactive surfactant molecules have long been used and characterized for a wide range of applications in industries, life science, and everyday life. Recently, new types of functional amphiphilic molecules have emerged that bear another function, for example, a light-absorbing action, or catalytic properties. However, the surfactant properties of these molecules remain to date essentially unknown. In this context, we investigated here the interfacial activity of photocatalytic surfactants base ...[more]

PMID: 35904352

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Project description:A family of complexes of the type [Ru(tpbn)(IP-R)(4-pic)]Cl2 (tbpn=2,2'-(4-(tert-butyl)pyridine-2,6-diyl)bis(1,8-napthyridine); 4-pic=4-picoline; IP-R=imidazo[4,5-f][1,10]phenanthroline attached to an aromatic group R for 2-8 and H for 1) were prepared as near-infrared (NIR) absorbing coordination complexes to test whether triplet intraligand excited states (3IL) of higher energy than the lowest-lying triplet metal-to-ligand charge transfer excited states (3MLCT) could effectively generate cytotoxic singlet oxygen (1O2) and elicit in vitro photodynamic therapy (PDT) effects. Aromatic groups ranged from benzene to anthracene, with corresponding triplet state energies that were all significantly higher (approximately 3.7-1.8 eV) than the 3MLCT state estimated at 1.5 eV. Complexes 1-8 absorbed NIR light, with their longest-wavelength peak maxima occurring near 725 nm that extended out to 800 nm. The 1O2 quantum yields for the aromatic-containing compounds were extremely small (ΦΔ=0.07), with correspondingly modest in vitro photocytotoxicities. All compounds were nontoxic without a light trigger, with dark EC50 values >60 μM and most values closer to 100 or greater. EC50 values with visible light were 5-6 (PI=15-20), 7-10 (PI=8-11), and 10-15 μM (PI=6-8) in SKMEL28, A375, and B16F10 cancer cell lines, respectively. With NIR light, these values were even less: 11-16 (PI=5-9), 16-50 (PI=2-6), and 15-19 μM (PI=4-6) in SKMEL28, A375, and B16F10 cancer cell lines, respectively. While measurable, the modest activities and absence of any trend between the 3IL energies and values for ΦΔ or PI demonstrate that 3IL states with energies above the lowest-lying 3MLCT states do not contribute to the overall excited state dynamics responsible for potent PDT effects in previous studies. Lowest-lying 3MLCT states in this family of NIR-absorbing photosensitizers do not produce the requisite 1O2 for effective in vitro photocytotoxic effects, underscoring the need to install 3IL states that are lower in energy than the lowest-lying 3MLCT states in order the create potent NIR-activatable Ru(II) complexes for PDT.

Dataset Information

Interfacial Characterization of Ruthenium-Based Amphiphilic Photosensitizers.

Publications

Interfacial Characterization of Ruthenium-Based Amphiphilic Photosensitizers.

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