Methylene-Bridged [6]CPP

Methylene-bridged [6]cycloparaphenylene (= CPP) (1), in which each benzene ring is tethered to its neighbor rings by methylene units, is the first methylene-bridged CPP synthesized by Itami et al.¹⁾ This skeleton is the substructure of Haeckelite nanotube and C₈₀ (Figure 1). 1 has narrower bandgap than [6]CPP by the enhancement of π-conjugation by methylene bridges. In addition, 1 forms a supramolecular structure by incorporation of small molecules into the cyclic skeleton. Furthermore, the methylene groups of this product can be selectively functionalized²⁾ (Figure 2) and further derivatization or extension of skeleton of 1 could be expected.

References

• 1) A Nonalternant Aromatic Belt: Methylene-Bridged [6]Cycloparaphenylene Synthesized from Pillar[6]arene
  • Y. Li, Y. Segawa, A. Yagi, K. Itami, J. Am. Chem. Soc. 2020, 142, 12850.
• 2) Towards the Highly Efficient Synthesis and Selective Methylation of C(sp³)-Bridged [6]Cycloparaphenylenes from Fluoren[3]arenes
  • X.-S. Du, D.-W. Zhang, Y. Guo, J. Li, Y. Han, C.-F. Chen, Angew. Chem. Int. Ed. 2021, 60, 13021.

Related Compounds

C2931

[5]Cycloparaphenylene

C3386

[6]Cycloparaphenylene

C3571

[7]Cycloparaphenylene

C3544

[8]Cycloparaphenylene

C3465

[9]Cycloparaphenylene

C3493

[10]Cycloparaphenylene

C3536

[11]Cycloparaphenylene

C2449

[12]Cycloparaphenylene

I1078

(6,6)Carbon Nanobelt Bis(tetrahydrofuran) Adduct

I0060

Iodomethane (stabilized with Copper chip)

P1008

Potassium tert-Butoxide

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