Krappmann Daniel, Hirsch Andreas
Department Chemistry and Pharmacy, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger Straße 10, 91058 Erlangen, Germany.
Beilstein J Org Chem. 2025 Apr 22;21:807-816. doi: 10.3762/bjoc.21.64. eCollection 2025.
We report the synthesis and characterization of heteroatom-incorporated norbornadiene (NBD) derivatives. Push-pull substitution on the 2 and 3 position as well as introduction of oxygen or nitrogen at position 7 of the NBD scaffold have led to the development of a new family of photoswitches. We studied the potential conversion of norbornadiene to quadricyclane (QC) isomers. As main investigation tools, UV-vis and NMR spectroscopy were utilized. We determined significant spectral features of the formed NBD species, including λ and λ values, all of which exhibit redshifts compared to their isocyclic counterparts. Additionally, the selected QC isomers were subjected to thermal and catalytic back-conversion studies.
我们报道了杂原子掺入的降冰片二烯（NBD）衍生物的合成与表征。在NBD骨架的2位和3位进行推挽取代以及在7位引入氧或氮，导致了一类新型光开关的开发。我们研究了降冰片二烯向四环烷（QC）异构体的潜在转化。作为主要的研究工具，我们使用了紫外可见光谱和核磁共振光谱。我们确定了所形成的NBD物种的重要光谱特征，包括λ和λ值，与它们的同环对应物相比，所有这些特征都表现出红移。此外，对选定的QC异构体进行了热和催化逆转化研究。
