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<p>Isomerically pure perylenetetracarboxylic propargyl ester derivatives (PPE-2 and PPE-4) were synthesized and characterized as energy-accepting molecular precursors for the construction of modular light-harvesting architectures. The electron-accepting perylenetetracarboxylic propargyl esters were coupled with electron-donor fluorene units via azide-alkyne cycloaddition (click) chemistry, affording donor–acceptor type conjugates (PMIDE-FL2, PTE-FL4). The UV–Vis absorption and photoluminescence measurements revealed absorption and emission maxima at 504 and 530&#xa0;nm for PPE-2 and PMIDE-FL2, respectively. Weaker electron-withdrawing perylene tetraester derivatives (PPE-4, PTE-FL4) have absorption and emission maxima at shorter wavelengths, at 472 and 503&#xa0;nm, respectively. Electrochemical characterization by cyclic voltammetry showed reduction potentials between -0.50 and -0.81&#xa0;V for all synthesized compounds which are related to the electron-accepting perylenetetracarboxylic units. Perylene monoimide diester derivatives exhibited less negative reduction potentials compared to the perylene tetraester analogues due to the higher electron-withdrawing ability of the perylene monoimide diester (PMIDE) derivatives. Thermal studies were performed by thermogravimetric analysis to investigate the thermal stability of the synthesized materials, and all compounds show high thermal stabilities with decomposition temperatures up to 250&#xa0;°C. Theoretical calculations on two donor–acceptor conjugates, namely PMIDE-FL2 and PTE-FL4, provided insight into their conformational preferences and electronic structures, indicating that the lowest-energy excitations are predominantly localized on the perylene core. Overall, PPE-2 and PPE-4 represent versatile and modular building-blocks for the development of perylene-based light-harvesting materials.</p> Graphical abstract <p></p>

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Synthesis, spectroscopic and structural characterization of bay-region brominated isomerically pure “clickable” perylenetetracarboxylic propargyl ester derivatives as functional light-harvesting precursors

  • 期刊论文

  • 发表日期：

    2026年4月13日

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  • Mohamad Abdulhakim Hassan Sawalha,
  • Saliha Ozdemir,
  • Mustafa Erkut Ozser

摘要

Isomerically pure perylenetetracarboxylic propargyl ester derivatives (PPE-2 and PPE-4) were synthesized and characterized as energy-accepting molecular precursors for the construction of modular light-harvesting architectures. The electron-accepting perylenetetracarboxylic propargyl esters were coupled with electron-donor fluorene units via azide-alkyne cycloaddition (click) chemistry, affording donor–acceptor type conjugates (PMIDE-FL2, PTE-FL4). The UV–Vis absorption and photoluminescence measurements revealed absorption and emission maxima at 504 and 530 nm for PPE-2 and PMIDE-FL2, respectively. Weaker electron-withdrawing perylene tetraester derivatives (PPE-4, PTE-FL4) have absorption and emission maxima at shorter wavelengths, at 472 and 503 nm, respectively. Electrochemical characterization by cyclic voltammetry showed reduction potentials between -0.50 and -0.81 V for all synthesized compounds which are related to the electron-accepting perylenetetracarboxylic units. Perylene monoimide diester derivatives exhibited less negative reduction potentials compared to the perylene tetraester analogues due to the higher electron-withdrawing ability of the perylene monoimide diester (PMIDE) derivatives. Thermal studies were performed by thermogravimetric analysis to investigate the thermal stability of the synthesized materials, and all compounds show high thermal stabilities with decomposition temperatures up to 250 °C. Theoretical calculations on two donor–acceptor conjugates, namely PMIDE-FL2 and PTE-FL4, provided insight into their conformational preferences and electronic structures, indicating that the lowest-energy excitations are predominantly localized on the perylene core. Overall, PPE-2 and PPE-4 represent versatile and modular building-blocks for the development of perylene-based light-harvesting materials.

Graphical abstract