NIR-absorbing donor–acceptor molecules based on fused thienopyrroloindole

Dyadishchev, Ivan V.; Bakirov, Artem V.; Peregudova, Svetlana M.; Ponomarenko, Sergei A.; Luponosov, Yuriy N.

doi:10.1016/j.mencom.2023.04.030

Cited by 4 publications

(1 citation statement)

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“…Push–pull conjugated small molecules are one of the most promising classes of organic semiconducting materials. Varying different structural parameters, such as the type of electron donor and electron acceptor units or their quantity and sequence within the molecule, allows fine-tuning both the spectral and other set of properties. − Push–pull chromophores have been widely used in biological and medical applications for the modulation of NO-mediated diseases, PDT, − and bioimaging. , One of the most promising electron donor blocks is triphenylamine, ,,, which has been used to obtain biocompatible organic materials. − Recently, we reported on push–pull molecules based on triphenylamine with both photovoltage and photocurrent photoresponses in biological electrolyte solution comparable to those of the human eye cones and rods. , …”

Section: Introductionmentioning

confidence: 99%

Nanoparticles of Push–Pull Triphenylamine-Based Molecules for Light-Controlled Stimulation of Neuronal Activity

Luponosov,

Solodukhin,

Aseyev

et al. 2024

ACS Biomater. Sci. Eng.

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Organic semiconductor materials with a unique set of properties are very attractive for interfacing biological objects and can be used for noninvasive therapy or detection of biological signals. Here, we describe the synthesis and investigation of a novel series of organic push−pull conjugated molecules with the starshaped architecture, consisting of triphenylamine as a branching electron donor core linked through the thiophene π-spacer to electron-withdrawing alkyl-dicyanovinyl groups. The molecules could form stable aqueous dispersions of nanoparticles (NPs) without the addition of any surfactants or amphiphilic polymer matrixes with the average size distribution varying from 40 to 120 nm and absorption spectra very similar to those of human eye retina pigments such as rods and green cones. Variation of the terminal alkyl chain length of the molecules forming NPs from 1 to 12 carbon atoms was found to be an efficient tool to modulate their lipophilic and biological properties. Possibilities of using the NPs as light nanoactuators in biological systems or as artificial pigments for therapy of degenerative retinal diseases were studied both on the model planar bilayer lipid membranes and on the rat cortical neurons. In the planar bilayer system, the photodynamic activity of these NPs led to photoinactivation of ion channels formed by pentadecapeptide gramicidin A. Treatment of rat cortical neurons with the NPs caused depolarization of cell membranes upon light irradiation, which could also be due to the photodynamic activity of the NPs. The results of the work gave more insight into the mechanisms of light-controlled stimulation of neuronal activity and for the first time showed that fine-tuning of the lipophilic affinity of NPs based on organic conjugated molecules is of high importance for creating a bioelectronic interface for biomedical applications.

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