Photochemical and photophysical behavior of indolyl anions in photostimulated intramolecular arylation reactions.

Org Biomol Chem

INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba, 5000, Argentina.

Published: December 2012

O-Arylation reaction is obtained when N-(2-halophenyl) indolo carboxamides are irradiated in a basic medium. On the basis of photochemical and photophysical experiments, we propose that 2-indolylbenzoxazole is formed by intramolecular electron transfer followed by fast dehalogenation of the halophenyl radical anion pendant moiety, finally a radical-radical collapse renders the observed product.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c2ob26698aDOI Listing

Publication Analysis

Top Keywords

photochemical photophysical
8
photophysical behavior
4
behavior indolyl
4
indolyl anions
4
anions photostimulated
4
photostimulated intramolecular
4
intramolecular arylation
4
arylation reactions
4
reactions o-arylation
4
o-arylation reaction
4

Similar Publications

Viridium: A Stable Radical and Its π-Dimerization.

J Am Chem Soc

January 2025

Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, Strasbourg 67000, France.

The discovery of a stable organic radical formed under mild, clean, and efficient light-mediated conditions is reported. The structure of the stable acridinium-based radical photoproduct was unambiguously established by single-crystal X-ray diffraction, mass spectrometry, and in solution by EPR, UV/vis, and NMR spectroscopies. The photochemical mechanism of its formation has been elucidated by photophysical experiments coupled with EPR experiments and theoretical investigations.

View Article and Find Full Text PDF

Finely Tailored Conjugated Small Molecular Nanoparticles for Near-Infrared Biomedical Applications.

Research (Wash D C)

January 2025

Frontiers Science Center for Flexible Electronics (FSCFE) & Institute of Flexible Electronics (IFE), Northwestern Polytechnical University, Xi'an 710072, P. R. China.

Near-infrared (NIR) phototheranostics (PTs) show higher tissue penetration depth, signal-to-noise ratio, and better biosafety than PTs in the ultraviolet and visible regions. However, their further advancement is severely hindered by poor performances and short-wavelength absorptions/emissions of PT agents. Among reported PT agents, conjugated small molecular nanoparticles (CSMNs) prepared from D-A-typed photoactive conjugated small molecules (CSMs) have greatly mediated this deadlock by their high photostability, distinct chemical structure, tunable absorption, intrinsic multifunctionality, and favorable biocompatibility, which endows CSMNs with more possibilities in biological applications.

View Article and Find Full Text PDF

Porphyrins bearing the unique 18π electron tetrapyrrolic macrocycles exhibit interesting photophysical and photochemical properties and have been considered as promising ligands for the construction of functionalized metal-organic frameworks (MOFs). The combination of porphyrin-type ligands with lanthanide metals featured with diverse coordination environments to realize the novel functions as well as the diversity of the MOF is thus attractive but challenging. Herein, an unprecedented porphyrin-based samarium MOF (Sm-BCPP) composed of a 5,10-bis(4-carboxyphenyl)-10,20-diphenyl porphyrin (HBCPP) ligand and samarium-formed one-dimensional clusters has been constructed via a solvothermal approach, and the synthesized Sm-BCPP has excellent chemical stabilities, exhibiting red luminescence.

View Article and Find Full Text PDF

Visible-Light-Fueled Polymerizations for 3D Printing.

Acc Chem Res

January 2025

Department of Chemistry, The University of Texas at Austin, 105 East 24th Street, Austin, Texas 78712, United States.

ConspectusLight-driven polymerizations and their application in 3D printing have revolutionized manufacturing across diverse sectors, from healthcare to fine arts. Despite the popularized notion that with 3D printing "imagination is the only limit", we and others in the scientific community have identified fundamental hurdles that restrict our capabilities in this space. Herein, we describe the group's efforts in developing photochemical systems that respond to nontraditional colors of light to elicit the rapid, spatiotemporally controlled formation of plastics.

View Article and Find Full Text PDF

Theoretical basis of all-optical modulation of a probe laser beam due to photothermal modulation of the aggregation state in organic dyes, with experimental proof of the principle.

Spectrochim Acta A Mol Biomol Spectrosc

December 2024

Anhembi Morumbi University (UAM), Rodovia Dr Altino Bondensan 500, São José dos Campos 12247-016, SP, Brazil; Center of Innovation, Technology and Education (CITE), Rodovia Dr Altino Bondensan 500, São José dos Campos 12247-016, SP, Brazil. Electronic address:

The inherent potential for self-assembly is a well-known attribute of organic dye molecules. This work takes advantage of the changes in dye photochemical and photophysical properties produced by the aggregation phenomenon, to investigate the behavior of all-optical modulation in molecular aggregates. The theoretical principles for a dual beam all-optical modulation, as well as the conception of an optical logic gate by exploring the aggregation phenomenon are discussed throughout the article.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!