Baig Noorullah, Shetty Suchetha, Bargakshatriya Rupa, Pramanik Sumit Kumar, Alameddine Bassam
Department of Mathematics and Natural Sciences, Gulf University for Science and Technology, Mubarak Al-Abdullah, Hawally 32093, Kuwait.
Functional Materials Group, Gulf University for Science and Technology, Mubarak Al-Abdullah, Hawally 32093, Kuwait.
ACS Omega. 2024 Aug 16;9(34):36732-36740. doi: 10.1021/acsomega.4c05526. eCollection 2024 Aug 27.
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-di-butylphenyl)acetylene with myriad brominated anthracene and pyrene surrogates, resulting in the formation of target molecules and , 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 (Δ) in the range of ∼2.88 to 2.97 eV for the monocylopentannulated PAHs , and between ∼2.23 to 2.41 eV for the dicyclopentannulated PAHs . Furthermore, the biomedical features of were investigated in cell-imaging experiments employing the RAW 264.7 macrophage cell line as a model system showing a high biocompatibility for , thus paving the way for its potential application in bioimaging. These findings underscore the significance of the target compounds as prominent AIEgens with exceptional photophysical properties and biocompatibility, therefore promoting them as valuable tools for bioimaging applications.
本文报道了通过钯催化的[3 + 2]环缩合反应合成各种多环芳烃（PAHs）。设计策略是使空间位阻较大的1,2 - 双（3,5 - 二丁基苯基）乙炔与多种溴化蒽和芘替代物反应，生成目标分子 和 ，它们在常用有机溶剂中表现出优异的溶解性，并在四氢呋喃和水的溶剂混合物中展现出显著的聚集诱导发光（AIE）特性。利用密度泛函理论（DFT）计算来验证目标分子的扭曲结构及其电子共轭，对于单环戊烷化的PAHs ，其HOMO - LUMO带隙（Δ）在约2.88至2.97 eV范围内，对于二环戊烷化的PAHs ，带隙在约2.23至2.41 eV之间。此外，在以RAW 264.7巨噬细胞系为模型系统的细胞成像实验中研究了 的生物医学特性，结果表明 具有高生物相容性，从而为其在生物成像中的潜在应用铺平了道路。这些发现强调了目标化合物作为具有优异光物理性质和生物相容性的突出聚集诱导发光体的重要性，因此推动它们成为生物成像应用中有价值的工具。
