In this communication, we demonstrate a novel approach to prepare a discrete dimer of chiral phthalocyanine (Pc) by exploiting the flexible molecular geometry of helicenes, which enables structural interlocking and strong aggregation tendency of Pcs. Synthesized [7]helicene-Pc hybrid molecular structure, zinc-[7]helicenocyanine (Zn-7HPc), exclusively forms a stable dimeric pair consisting of two homochiral molecules. The dimerization constants were estimated to be as high as 8.96×10⁶ M⁻¹ and 3.42×10⁷ M⁻¹ in THF and DMSO, respectively, indicating remarkable stability of dimer. In addition, Zn-7HPc exhibited chiral self-sorting behavior, which resulted in preferential formation of a homochiral dimer also in the racemic sample. Two phthalocyanine subunits in the dimeric form strongly communicate with each other as revealed by a large comproportionation constant and observation of an IV-CT band for the thermodynamically stable mixed-valence state.

中文翻译：

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锌-[7]螺旋花青及其离散的π-堆叠同手性二聚体

在本次交流中，我们展示了一种通过利用螺旋烯的灵活分子几何形状来制备手性酞菁 (Pc) 离散二聚体的新方法，该方法能够实现 Pcs 的结构互锁和强聚集趋势。合成的 [7] helicene-Pc 杂化分子结构，锌-[7] helicenocyanine (Zn-7HPc)，专门形成由两个同手性分子组成的稳定二聚体对。估计二聚化常数高达8.96×10 ⁶  M ^-1和3.42×10 ⁷  M ^-1分别在 THF 和 DMSO 中，表明二聚体具有显着的稳定性。此外，Zn-7HPc 表现出手性自分选行为，这导致在外消旋样品中也优先形成同手性二聚体。二聚体形式的两个酞菁亚基彼此强烈地相互联系，这通过大的比例常数和对热力学稳定混合价态的 IV-CT 带的观察来揭示。