含二茂铁基团的芴-苯共轭化合物的合成及其性能研究

通过Suzuki偶联反应合成了二茂铁基团存在于侧链、主链和端基的苯-芴共轭化合物6、7和8,并通过 NMR和MS等表征手段对其结构进行了确认.共轭化合物中的二茂铁基团通过分子内的光致电子转移过程使6、7和8在溶液状态下的荧光猝灭.当向其溶液中加入氧化剂KMnO₄后,溶液的荧光强度显著增强,最大可增至75倍.荧光增强的幅度、对氧化剂的响应时间等性质受二茂铁在共轭化合物中的位置以及个数的影响.实验结果表明, 分子中含有一个二茂铁基团其荧光增强是线型增长的,响应时间也较短;当共轭分子中含有两个二茂铁基团时,其荧光强度的增长成二次函数关系,且其响应时间也较长. 

Synthesis and Their Property of Fluorene-Phenyls Conjugated Molecules Containing Ferrocene

Conjugated compounds with ferrocene as the side group (6), in the backbone (7) and as the end groups (8) were synthesized by Suzuki coupling reaction. The chemical structures of these compounds were verified by NMR and MS. The fluorescence of 6, 7 and 8 in THF were strongly quenched by ferrocene via an intramolecular photoinduced electron transfer (PET) process. However, adding oxidant such as dilute solution of KMnO₄ a.q. into the solution of 6, 7 and 8, respectively, the fluorescent intensity of these compounds were increased and can be up to 75 times. The fluorescence amplification and response time to oxidant were affected by the position and numbers of ferrocene in these conjugated compounds. The results show that fluorescence enhancement is linear with concentration of oxidant and rapidly responds to oxidant when one ferrocene exists in conjugated structures. Response time becomes slow and fluorescence enhancement is quadratic with concentration of oxidant when there are two ferrocenes in one conjugated molecule.