Synthesis of a Substituted [10]Cycloparaphenylene through [2+2+2] Cycloaddition

Herein, we report the synthesis and investigation of a substituted [10]cycloparaphenylene (CPP) incorporating diethylphthalane unit. An efficient strategy relying on symmetric built-up starting with propargyl ether as [2+2+2] cycloaddition precursor was developed. The straightforward required overcoming unexpected obstacles within cycloaddition, protection aromatization. These results give valuable insights for accessing CPPs highly subunits. Finally, seven-step an overall yield 8 % provided target nanoring, including good to excellent yields critical macrocyclization synthesized nanohoop exhibits hypsochromic shift in fluorescence absorption, compared unsubstituted [10]CPP. This observation is proposedly caused by increased torsion angle between bivalent phenyl moieties adjacent units.