We have designed and synthesized a novel amide-linked bisporphyrin with a 2-naphthalenecarboxamide substituent on the linker. The chirality sensing ability of this zinc porphyrinate towards chiral monoamines has been examined. Circular dichroism studies indicate chirality transfer from chiral monoamines to the corresponding host–guest complexes. Interestingly, when optically pure 1-(1-naphthyl)ethylamine is used as a guest, stoichiometrically controlled chirality inversion occurs in the formation of the corresponding zinc bisporphyrinate–monoamine complexes. Both CD and NMR spectra indicate that 1 : 1 and 1 : 2 complexes are formed in solution. DFT calculations suggest that steric interactions between the substituent of the linker and the guest in the 1 : 2 complex are responsible for this unprecedented observation. Our studies provide a unique bisporphyrin system for demonstrating that chirality transfer to the host can be tuned by changing the substituent of the linker.

中文翻译：

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双卟啉锌-单胺复合物的化学计量控制手性反转†

我们设计并合成了一种新型的酰胺连接的双卟啉，其连接子上带有一个2-萘甲酰胺取代基。已经检查了该卟啉锌对手性单胺的手性感测能力。圆二色性研究表明，手性从手性单胺转移到相应的宿主-客体复合物中。有趣的是，当使用光学纯的1-（1-萘基）乙胺作为客体时，在相应的双卟啉锌-单胺络合物的形成中发生了化学计量控制的手性反转。CD谱和NMR谱均表明在溶液中形成1∶1和1∶2的络合物。DFT计算表明，接头的取代基与1：2络合物中的客体之间的空间相互作用是造成这种空前观察的原因。