Exploring Cyclopentannulation as an Effective Synthetic Tool to Design Polycyclic Aromatic Hydrocarbon AIEgens for Bioimaging.

ABSTRACT: Synthesis of various polycyclic aromatic hydrocarbons (PAHs) from a palladium-catalyzed [3 + 2] cyclocondensation reaction is reported herein. The design strategy consisted of reacting the sterically hindered 1,2-bis(3,5-ditert-butylphenyl)acetylene 2 with myriad brominated anthracene and pyrene surrogates, resulting in the formation of target molecules MCP1-2 and DCP1-3, which exhibited excellent solubility in commonly used organic solvents and unveiled prominent aggregation-induced emission (AIE) characteristics in tetrahydrofuran and water solvent mixtures. Calculations using density functional theory (DFT) were utilized to validate both the contorted structures of the target molecules and their electronic conjugation featuring HOMO-LUMO band gaps (ΔE)

SUBMITTER: Baig N 

PROVIDER: S-EPMC11360036 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature