Silyl-bridged dimers of a ppy-BMes(2) (ppy = 2-phenylpyridine, Mes = mesityl) photochrome were found to undergo photochromic switching involving a single boryl unit only. A through-space intramolecular energy transfer was found to be responsible for the single-chromophore isomerization phenomenon and fluorescence quenching. Steric congestion in the diboryl molecules was found to have an impact on photoisomerization quantum efficiency.
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http://dx.doi.org/10.1021/ol102319t | DOI Listing |
Acc Chem Res
February 2025
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing 100084, China.
ConspectusPyridine is a crucial heterocyclic compound in organic chemistry. Typically, the pyridine motif behaves as an N-nucleophile and an electron-deficient aromatic ring. Transforming the pyridine ring into an electron-rich system that exhibits reactivity contrary to classical expectations could unveil new opportunities in pyridine chemistry.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing, 100084, P.R. China.
The in-depth research on the charge transport properties of BN-embedded polycyclic aromatic hydrocarbons (BN-PAHs) still lags far behind studies of their emitting properties. Herein, we report the successfully synthesis of novel ladder-type BN-PAHs (BCNL1 and BCNL2) featuring a highly ordered BCN acene unit, achieved via a nitrogen-directed tandem C-H borylation. Single-crystal X-ray diffraction analysis unambiguously revealed their unique and compact herringbone packing structures.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, David Brewster Road. Edinburgh, EH9 3FJ, UK.
J Am Chem Soc
November 2024
Department of Chemistry, University of California Berkeley, Berkeley, California 94720, United States.
The functionalization of C-H bonds enables the modification of complex molecules, often with the intention of forming compound libraries. The borylation of aryl C-H bonds is a widely used class of C-H bond functionalization, and conventional catalyst systems for the borylation of C-H bonds consist of an iridium source and an ,-ligand, in conjunction with pinacolborane, to form the active iridium(III) tris(boryl) catalyst. These multicomponent catalyst systems complicate borylation reactions at large and small scales, due to the air sensitivity of the most common iridium precursor [Ir(cod)OMe], and, particularly on small scale, the challenges associated with dispensing multiple components with differing solubilities or that are air-sensitive.
View Article and Find Full Text PDFPrecis Chem
January 2024
State Key Laboratory of Synthetic Chemistry, HKU-CAS Joint Laboratory on New Materials and Department of Chemistry, The University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong, China.
The precise synthesis of helicenes with topologically defined length and specific heteroatomic perturbation in the screw-like conjugated skeletons plays an emerging role in the manipulation of chiral materials. Facile, selective, and programmable routes to helicenes or heterohelicenes are highly desirable yet challenging for structure-chiroptical property relationship studies. Herein, we report the synthesis and characterization of NBN-doped helicenes with boron atoms in the inner rims, enabled by the highly regioselective one-pot borylation of rationally designed precursors with, namely, fold-in or pan-out manner.
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