Kakimoto Yuna, Ikemura Ryoya, Imai Yoshitane, Tohnai Norimitsu, Yamazaki Shoko, Nakata Eiji, Takashima Hiroshi
Department of Chemistry, Biology and Environmental Science, Faculty of Science, Nara Women's University Nara 630-8506 Japan
Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University Osaka 577-8502 Japan.
RSC Adv. 2023 Jan 11;13(3):1914-1922. doi: 10.1039/d2ra07971b. eCollection 2023 Jan 6.
In this study, we report circularly polarised luminescence (CPL)-active molecules that exhibit high fluorescence quantum yields in the solid state. We developed anthracene derivatives with substituents at the 9 and 10 positions, such as ethyl(anthracene-9-carbonyl)glycinate (9AnGlyEt), -butylanthracene-9-carboxamide (9AnB), -benzylanthracene-9-carboxamide (9AnPh), and , -dibutylanthracene-9,10-dicarboxamide (9,10AnB). These compounds were complexed with γ-cyclodextrin (γ-CD) in the solid state by grinding, and the fluorescence properties of the resulting γ-CD complexes were investigated. The fluorescence quantum yields were enhanced after γ-CD complexation. Among the prepared γ-CD complexes, 9AnGlyEt/γ-CD had the highest fluorescence quantum yield ( = 0.35), which was enhanced up to 5.8 times after γ-CD complexation. This was probably due to the interaction between the two anthracene molecules in the γ-CD cavity, which prevented fluorescence quenching caused by aggregation of the compounds. Positive CPL of = 1.3 × 10 was observed for 9AnGlyEt/γ-CD based on its excimer emission.
在本研究中,我们报道了在固态下表现出高荧光量子产率的圆偏振发光(CPL)活性分子。我们开发了在9位和10位带有取代基的蒽衍生物,如乙基(蒽-9-羰基)甘氨酸酯(9AnGlyEt)、9-丁基蒽甲酰胺(9AnB)、9-苄基蒽甲酰胺(9AnPh)以及9,10-二丁基蒽-9,10-二甲酰胺(9,10AnB)。这些化合物通过研磨在固态下与γ-环糊精(γ-CD)形成复合物,并对所得γ-CD复合物的荧光性质进行了研究。γ-CD络合后荧光量子产率提高。在所制备的γ-CD复合物中,9AnGlyEt/γ-CD具有最高的荧光量子产率(Φ = 0.35),γ-CD络合后提高了5.8倍。这可能是由于γ-CD腔内两个蒽分子之间的相互作用,阻止了化合物聚集导致的荧光猝灭。基于其准分子发射,9AnGlyEt/γ-CD观察到正的圆偏振发光(g lum)为1.3×10。