Intramolecular hydrogen bonding as a synthetic tool to induce chemical selectivity in acid catalyzed porphyrin synthesis.

Chem Commun (Camb)

Center for Bio-Inspired Solar Fuel Production, Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287, USA.

Published: May 2012

A straightforward procedure based on the formation of intramolecular hydrogen bonds to impart selectivity in the preparation of multi-functionalized porphyrins has been developed. To illustrate the concept, the synthesis of a biomimetic artificial photosynthetic model able to undergo electron and proton transfer reactions upon irradiation is reported.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c2cc31228jDOI Listing

Publication Analysis

Top Keywords

intramolecular hydrogen
8
hydrogen bonding
4
bonding synthetic
4
synthetic tool
4
tool induce
4
induce chemical
4
chemical selectivity
4
selectivity acid
4
acid catalyzed
4
catalyzed porphyrin
4

Similar Publications

Ingeniously regulating the conformational equilibrium and ESPT mechanism of HBT-DPI by solvent environment: A novel perspective.

Spectrochim Acta A Mol Biomol Spectrosc

January 2025

Jilin Key Laboratory of Solid-State Laser Technology and Application, School of Physics, Changchun University of Science and Technology, Changchun 130022 China. Electronic address:

HBT-DPI was a single-molecule multi-conformational fluorescent material and had unique applications for hydrophobic/hydrophilic mapping on large-scale heterogeneous surfaces. In this paper, the different proton transfer processes and luminescence mechanisms of HBT-DPI in Dichloromethane (DCM, no hydrogen bond (HB) receptor) and N, N-Dimethylformamide (DMF, HB receptor) solvents were systematically studied. Using the quantum chemistry method, the stable structures of HBT-DPI in two solvents were determined based on the Boltzmann distribution.

View Article and Find Full Text PDF

Elaborating H-bonding effect and excited state intramolecular proton transfer of 2-(2-hydroxyphenyl)benzothiazole based D-π-A fluorescent dye.

Phys Chem Chem Phys

January 2025

Key Laboratory of Soft Chemistry and Functional Materials of MOE, School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China.

2-(2-Hydroxyphenyl)benzothiazole (HBT) derivatives with donor-π-acceptor (D-π-A) structure have received extensive attention as a class of excited state intramolecular proton transfer (ESIPT) compounds in the fields of biochemistry and photochemistry. The effects of electron-donors (triphenylamine and anthracenyl), the position of substituents and solvent polarity on the fluorescence properties and ESIPT mechanisms of HBT derivatives were investigated through time-dependent density functional theory (TDDFT) calculations. Potential energy curves (PECs) and frontier molecular orbitals (FMOs) reveal that the introduction of the triphenylamine group on the benzene ring enhances intramolecular HB, thereby benefiting the ESIPT process.

View Article and Find Full Text PDF

(1,2)--Aminoindanol and (1,2)--aminoindanol, denoted as -AI and -AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in -AI, which is absent in -AI. They also differ by the number of conformers under supersonic jet conditions, one for -AI and two for -AI. One-photon and resonance-enhanced two-photon photoelectron circular dichroism (PECD) spectra are obtained for the two molecules.

View Article and Find Full Text PDF

Noncovalent carbon bonding (C-bonding), a recently explored σ-hole interaction, has primarily been characterized through X-ray structural and computational studies. Evidence of C-bonds in solution is scarce, especially in highly polar solvents like DMSO where solvation effects typically overshadow weak non-covalent interactions. In this work, we present three novel spiroisatin-based -acyl hydrazones (1-3) in which C-bonds play a critical role in stabilizing the conformation in solution.

View Article and Find Full Text PDF

4'-Selective alkylation of nucleosides has been recognized as one of the ideal and straightforward approaches to chemically modified nucleosides, but such a transformation has been scarce and less explored. In this Letter, we combine a visible-light-mediated photoredox catalysis and hydrogen atom transfer (HAT) auxiliary to achieve β-C(sp)-H alkylation of alcohol on tetrahydrofurfuryl alcohol scaffolds and exploit it for 4'-selective alkylation of nucleosides. The reaction involves an intramolecular 1,5-HAT process and stereocontrolled Giese addition of the resultant radicals.

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!