An efficient in situ generation of ortho-quinodimethane (o-QDM) from 2-methyl-3,5-dinitrobenzoic acid through N-Heterocyclic Carbene (NHC) catalysis, which underwent a formal [4 + 2] annulation with activated C=O (or C=N) bonds for the assembly of isoquinolinone and isochromanone scaffolds, was disclosed. This method features challenging direct functionalizations of C(sp3)-H bond, readily available starting materials, mild reaction conditions and good yields.

An NHC-catalyzed hetero-Diels-Alder and isomerization process of chalcones with allenoates was discovered, which furnished highly functionalized multisubstituted pyranyl carboxylates successfully. This method features a convergent assembly, mild reaction conditions, moderate to good yields, and high atom economy.

An asymmetric assembly of naphthopyran was realized via the N-heterocyclic carbene (NHC)-catalyzed formal [3 + 3] annulation of bromoenal and β-tetralone. The key advantages of this protocol include ready availability of starting materials, mild reaction conditions, good yields.

It is still a challenging work of developing near-infrared (NIR) uorescence dyes with excellent optical properties. Herein, we synthesized a series of NIR aza-BODIPY uorescence dyes with electronic push-pull system and further investigated their photophysical properties, photostability, and application in cellular imaging. It was found that introducing electron-withdrawing groups (EWGs) on the para-position of aza-BODIPY 1,7-phenyls not only leads to the signi cant redshift of absorption and uorescence emission bands of aza-BODIPY dyes but also increases their uorescence quantum yield and photostablility. The DFT calculations and cyclic voltammetry measurements proved that introducing EWGs on para-position of 1,7-phenyls can decrease the energy level difference between HOMO and LUMO, resulting in the redshift of maximum absorption and emission wavelengths. On the basis of the feasible experiment results of cellular imaging and cytotoxicity assay, it is expected that the optimized aza-BODIPY dyes have a bright application prospect for in-vivo cellular or tissue imaging.

It is still a challenging work of developing near-infrared (NIR) fluorescence dyes with excellent optical properties. Herein, we synthesized a series of NIR aza-BODIPY fluorescence dyes with electronic push-pull system and further investigated their photophysical properties, photostability, and application in cellular imaging. It was found that introducing electron-withdrawing groups (EWGs) on the para-position of aza-BODIPY 1,7-phenyls not only leads to the significant redshift of absorption and fluorescence emission bands of aza-BODIPY dyes but also increases their fluorescence quantum yield and photostablility. The DFT calculations and cyclic voltammetry measurements proved that introducing EWGs on para-position of 1,7-phenyls can decrease the energy level difference between HOMO and LUMO, resulting in the redshift of maximum absorption and emission wavelengths. On the basis of the feasible experiment results of cellular imaging and cytotoxicity assay, it is expected that the optimized aza-BODIPY dyes have a bright application prospect for in-vivo cellular or tissue imaging.