Three new distinct NIR α,α-NH-bridged BODIPY dimers were prepared by a direct nucleophilic substitution reaction. The synergistic effects of the nitrogen bridges and strong excitonic coupling between each BODIPY unit play major roles in enhancing the delocalization of an electron spin over the entire BODIPY dimers. The formed aminyl radical dimer showed an absorption maximum at 1040 nm.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d4cc00878b | DOI Listing |
Org Lett
January 2025
DFG Cluster of Excellence livMatS @FIT, Institute of Organic Chemistry, Albertstraße 21, 79104 Freiburg (Breisgau), Germany.
facile access to -heteroaryl-fused bis-BODIPY scaffolds has been developed. A BODIPY dimer with an α,α-amine linker serves as a starting material to obtain pyrrole- and pyridine-fused BODIPYs, either by direct oxidation or by oxidative condensation with an aldehyde building block. Both species mark antipodal conjugative coupling conditions that result in distinct spectral outcomes.
View Article and Find Full Text PDFJ Org Chem
December 2024
Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
Herein, we report the synthesis of novel dimeric urea-bridged BODIPY-carbohydrate conjugates, which display circularly polarized luminescence (CPL). The dimers are composed of diastereomerically pure, axially chiral (P or M) BODIPY monomers containing a pendant glucose (d- or l-) unit. The latter was intended to add chirality, biocompatibility, and enhanced water solubility and facilitate the chromatographic resolution of the intermediate atropisomers.
View Article and Find Full Text PDFLangmuir
December 2024
CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology (NCNST), Beijing 100190, P. R. China.
Molecules
November 2024
Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, Poland.
Synthesis, photochemical properties, liposomal encapsulation, and in vitro photodynamic activity studies of novel BODIPY dimer connected at positions and its brominated and iodinated analogs were described. UV-Vis measurements indicated that the dimeric structure of obtained BODIPYs did not significantly influence the positions of the absorption maxima. Emission properties and singlet oxygen generation studies revealed a strong heavy atom effect of brominated and iodinated BODIPY dimers, manifested by fluorescence intensity reduction and increased singlet oxygen generation ability compared to analog without halogen atoms.
View Article and Find Full Text PDFDalton Trans
January 2025
Jiangsu Co-innovation Center of Efficient Processing and Utilization of Forest Resources, Key Laboratory of Forestry Genetics & Biotechnology of Ministry of Education, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, P. R. China.
Four BODIPY dyes (6a-6d) with electron-donating or electron-withdrawing groups at the -position were synthesized by the Sonogashira coupling reaction of 2,5-diethynylthieno[3,2-]thiophene with mono-iodo-BODIPY moieties. All compounds were fully characterized by H NMR and MALDI-TOF MS. Their photophysical and electrochemical properties were studied by UV-visible absorption spectroscopy, steady-state and time-resolved fluorescence spectroscopy, two-photon excitation spectroscopy and cyclic voltammetry.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!