Synthesis of Novel Biocompatible Thienopyrimidine Chromophores with Aggregation-Induced Emission Sensitive to Molecular Aggregation

Abstract

Biocompatible luminogens with aggregation-induced emission (AIE) have several applications in the biology field, such as in detecting biomacromolecules bioprobes and in bio-imaging. Due to their bioactivities and light-emitting properties, many heterocyclic compounds are good candidates for such applications. However, heterocyclic π-conjugated systems with AIE behavior remain rare as strong intermolecular π–π interactions usually quench their emission. In this work, new thienopyrimidine heterocyclic compounds were synthesized and their structures were verified by elemental analysis and Fourier transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and 13C NMR spectra. The photophysical properties of some compounds were investigated in the solution and solid states. Density functional theory calculations were also performed to confirm the observed photophysical properties of the compounds. The studied dyes displayed AIE properties with spectral shapes related to the aggregate structure and a quantum yield up to 10.8%. The emission efficiency of the powder is attributed to the incorporation of multiply rotatable and twisted aryl groups to the fused heterocyclic moieties. The dyes also showed high thermal stability and potent antimicrobial activities against numerous bacterial and fungal strains. Additionally, the cytotoxicity of the new compounds was evaluated against the Caco-2 cell line, and molecular docking was used to investigate the binding conformation of the most effective compound with the MNK2 enzyme. Therefore, the presented structures may potentially be used for bioapplications.

Recent trends in molecular aggregates: An exploration of biomedicine

“…Thienopyrimidine derivatives (55, 56) are bioactive heterocyclic AIEgens. [ 89 ] Thienopyrimidine was reported to bind to the ATP‐binding pocket of MAP kinase signal integrating kinases (MNKs). AIE and solid‐state emission in the range of 400–560 nm was achieved through the incorporation of various rotatable aryl moieties to thienopyrimidine.…”

From Blue to Green Photoluminescence: Design, Synthesis, and DFT Calculations of Heterocyclic Compounds Containing Chromenothienopyrimidine Moiety

“…[3,5] We have also reported some pyrimidine derivatives having both biological activities and luminescence efficiency. [8,9] Coumarin is also regarded as a wealthy heterocyclic scaffold for medicinal chemistry, and it is widely used in the development of new biologically active compounds. [10] Moreover, the coumarin nucleus has been widely used in the design of photo-and electroactive materials, [11,12] including fluorescent chemosensors, [13] laser dyes, [14] and light-harvesting dyes for dye-sensitized solar cells.…”

“…[38][39][40] Green emission is also one of the basic colors to realize the full-color emission. Based on the concerns expressed above, and in continuation of our prior projects, [2][3][4][5][6][7][8] we present here a synthetic method for some novel coumarinpyrimidine hybrids. The photophysical properties of some substances in the solution forms were investigated.…”

“…Compounds bearing the pyrimidine moiety exhibit a wide spectrum of pharmacological activities. [1] Furthermore, various pyrimidine analogs have been discovered to have antibacterial, [2,3] antifungal, [4,5] anticancer agents, [6][7][8] antiinflammatory. [3,5] We have also reported some pyrimidine derivatives having both biological activities and luminescence efficiency.…”

“…Furthermore, various pyrimidine analogs have been discovered to have antibacterial, [2,3] antifungal, [4,5] anticancer agents, [6–8] anti‐inflammatory [3,5] . We have also reported some pyrimidine derivatives having both biological activities and luminescence efficiency [8,9] . Coumarin is also regarded as a wealthy heterocyclic scaffold for medicinal chemistry, and it is widely used in the development of new biologically active compounds [10] .…”