Kalarus Paweł, Szlapa-Kula Agata, Filapek Michał, Kula Sławomir
Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Szkolna 9 St., 40-007 Katowice, Poland.
Molecules. 2025 Apr 25;30(9):1924. doi: 10.3390/molecules30091924.
Fluorene has been an extremely valued building block for many chemical compounds for a number of years. As a result, it is possible to design and obtain compounds with precisely defined physicochemical properties adapted to selected applications. An extremely interesting derivative of fluorene, which has been enjoying increasing interest in recent years, is dibenzofulvene (DBF) and its further structural modifications. So far, a number of dibenzofulvene derivatives have been described in the literature. Many of the presented DBFs are extremely structurally complex, which is why the influence of substituents on the physicochemical properties of the final compounds is not easy to determine unequivocally. Therefore, in this article, an attempt was made to explain the influence of N-donor substituents on selected physicochemical properties of dibenzofulvene derivatives (A-1-A-6). Moreover, these properties were compared to the results obtained for unsubstituted fluorene. The studies conducted showed that small modifications of the fluorene structure towards dibenzofulvene derivatives significantly change the absorption and emission properties of the final compounds. Importantly, the abovementioned structural modifications strongly affect the electrochemical properties, significantly reducing the energy gap and causing the oxidation potential to decrease to 0.18-0.42 V. Moreover, the process itself becomes fully reversible. The experimentally determined values coincide with those obtained theoretically via DFT calculations.
多年来，芴一直是许多化合物中极为重要的结构单元。因此，能够设计并获得具有精确界定的物理化学性质、适用于特定应用的化合物。芴的一种极其有趣的衍生物，近年来受到越来越多的关注，即二苯并富烯（DBF）及其进一步的结构修饰。到目前为止，文献中已经描述了许多二苯并富烯衍生物。所呈现的许多DBF在结构上极其复杂，这就是为什么取代基对最终化合物物理化学性质的影响不容易明确确定的原因。因此，在本文中，试图解释含氮供体取代基对二苯并富烯衍生物（A-1 - A-6）选定物理化学性质的影响。此外，将这些性质与未取代芴所获得的结果进行了比较。进行的研究表明，芴结构向二苯并富烯衍生物的微小修饰显著改变了最终化合物的吸收和发射性质。重要的是，上述结构修饰强烈影响电化学性质，显著降低能隙并使氧化电位降至0.18 - 0.42 V。此外，该过程本身变得完全可逆。实验测定的值与通过密度泛函理论（DFT）计算理论上获得的值一致。
