The synthesis and characterization of a series of 3- or 4-substituted 1,8-naphthalic anhydride compounds, and their organophosphorus analogues, bearing a cyclic diketophosphanyl moiety, are reported. The new anhydrides have been synthesized by Stille coupling with a variety of aryl groups with different donor strengths from the corresponding 3- and 4-bromo substituted anhydrides, respectively. The thienyl- and (dimethylamino)phenyl-substituted anhydrides have moreover been used as precursors for the synthesis of the corresponding diketophosphanyl derivatives by reaction with MesP(SiMe₃)₂. The photophysical and electrochemical properties of the new compounds have been studied. Density functional theory (DFT) and time-dependent DFT calculations have been carried out in order to rationalize their electronic structures and electronic absorption properties. The low-energy absorption bands exhibit mainly (π → π*) charge-transfer character from the aryl moieties to the anhydride or diketophosphanyl core, respectively. In the thiophene-containing diketophosphanyl compounds the low-energy absorption also shows some electron-transfer features from the phosphorus moiety (MesP) to the core. The charge-transfer nature of the transition has been confirmed by solvatochromic absorption and emission studies.

中文翻译：

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具有1,8-萘酐或二酮膦烷基单元的电子接受性π共轭物质

报道了带有环二酮膦基部分的一系列3-或4-取代的1,8-萘酐化合物及其有机磷类似物的合成和表征。新的酸酐是通过Stille与相应的3-和4-溴取代的酸酐分别与具有不同施主强度的各种芳基偶联而合成的。此外，噻吩基和（二甲基氨基）苯基取代的酸酐已经用作通过与MesP（SiMe ₃）₂反应合成相应的二酮膦基衍生物的前体。。已经研究了新化合物的光物理和电化学性质。为了使它们的电子结构和电子吸收特性合理化，已经进行了密度泛函理论（DFT）和随时间变化的DFT计算。低能吸收带主要表现出从芳基部分到酸酐或二酮膦烷基核心的（π→π*）电荷转移特性。在含噻吩的二酮膦烷基化合物中，低能吸收也显示出从磷部分（MesP）到核的一些电子转移特征。过渡变色的电荷转移性质已通过溶剂变色吸收和发射研究得到证实。