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1.
J Mater Chem B ; 2024 Jul 23.
Artigo em Inglês | MEDLINE | ID: mdl-39041337

RESUMO

As the field of preclinical research on photosensitizers (PSs) for anticancer photodynamic therapy (PDT) continues to expand, a focused effort is underway to develop agents with innovative molecular structures that offer enhanced targeting, selectivity, activation, and imaging capabilities. In this context, we introduce two new heavy-atom-free PSs, DBXI and DBAI, characterized by a twisted π-conjugation framework. This innovative approach enhances the spin-orbit coupling (SOC) between the singlet excited state (S1) and the triplet state (T1), resulting in improved and efficient intersystem crossing (ISC). Both PSs are highly effective in producing reactive oxygen species (ROS), including singlet oxygen and/or superoxide species. Additionally, they also demonstrate remarkably strong fluorescence emission. Indeed, in addition to providing exceptional photocytotoxicity, this emissive feature, generally lacking in other reported structures, allows for the precise monitoring of the PSs' distribution within specific cellular organelles even at nanomolar concentrations. These findings underscore the dual functionality of these PSs, serving as both fluorescent imaging probes and light-activated therapeutic agents, emphasizing their potential as versatile and multifunctional tools in the field of PDT.

2.
J Org Chem ; 89(12): 8407-8419, 2024 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-38853362

RESUMO

This work investigates the electron-donating capabilities of two 10-π electron nitrogen bridgehead bicyclic [5,6]-fused ring systems, imidazo[1,2-a]pyridine and imidazo[1,5-a]pyridine rings. Eight compounds with varying positions of electron-withdrawing moieties (TCF or DCI) coupled to the imidazopyridine ring were synthesized and studied. DCI-containing compounds (Ib-IVb) exhibited a purely dipolar nature with broad absorption bands, weak fluorescence, large Stokes shifts, and strong solvatochromism. In contrast, TCF-containing compounds (Ia-IVa) demonstrated diverse properties. Imidazo[1,2-a]pyridine derivatives Ia and IIa were purely dipolar, while imidazo[1,5-a]pyridine derivatives IIIa and IVa displayed a cyanine-like character with intense absorption and higher quantum yields of emission. The observed gradual red shift in optical properties with changing electron-donor groups (IIb < Ib < IIIb < IVb) and (IIa < Ia < IIIa < IVa) underscores the stronger electron-donor character of imidazo[1,5-a]pyridine compared to that of imidazo[1,2-a]pyridine. Furthermore, crystalline powders of imidazo[1,2-a]pyridine derivatives exhibited fluorescence despite minimal emission in solution. Two compounds (Ib and IVa) were successfully formulated into nanoparticles for potential in vivo imaging applications in zebrafish embryos.

3.
Chemistry ; 30(27): e202400191, 2024 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-38498874

RESUMO

Controlling the formation of photoexcited triplet states is critical for many (photo)chemical and physical applications. Here, we demonstrate that a permanent out-of-plane distortion of the benzothioxanthene imide (BTI) dye promotes intersystem crossing by increasing spin-orbit coupling. This manipulation was achieved through a subtle chemical modification, specifically the bay-area methylation. Consequently, this simple yet efficient approach expands the catalog of known molecular engineering strategies for synthesizing heavy atom-free, dual redox-active, yet still emissive and synthetically accessible photosensitizers.

4.
J Comput Chem ; 45(12): 834-842, 2024 May 05.
Artigo em Inglês | MEDLINE | ID: mdl-38146809

RESUMO

In this work, we investigate the spectroscopic properties of photochromic alexandrite and cordierite by TD-DFT. The objective is to assess the TD-DFT for the simulation of pleochroism (change of color depending on the crystallographic direction of the observation) and the change of color as a function of the light source. For these simulations, we compared an embedding where dangling bonds are saturated by hydrogen atoms and an electrostatic embedding. The electrostatic embedding provided numerically more stable results and allowed a good reproduction of the pleochroism of cordierite, based on a Fe2+-Fe3+ intervalence charge transfer transition. However, the pleochroism of alexandrite is not as well reproduced, suggesting that TD-DFT has some difficulties to reproduce the anisotropy of the transition dipole moment, an aspect that is not deeply documented in the literature.

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