[5]cycloparaphenylene

Base Information

• Chemical Name: [5]cycloparaphenylene
• CAS No.: 96100-94-6
• Molecular Formula: C₃₀H₂₀
• Molecular Weight: 380.489
• Mol file: 96100-94-6.mol

Synonyms:

Chemical Property of [5]cycloparaphenylene

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

[5]Cycloparaphenylene >95.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: [5]Cycloparaphenylene ([5]CPP) is a highly strained carbon nanohoop that serves as a fragment of buckminsterfullerene (C₆₀), the equatorial segment of C₇₀, and the repeating unit of a [5,5] armchair carbon nanotube. With a calculated strain energy of 119 kcal mol^?1 and severely distorted benzene rings, it exhibits remarkable properties, including a narrow HOMO/LUMO gap, high solubility, and pseudoreversible redox behavior, making it a promising candidate for organic electronics. Its synthesis involves a mild, high-yielding room-temperature macrocyclization of a diboronate precursor, followed by single-electron reduction and elimination. Additionally, [5]CPP can undergo site-selective bromination, enabling late-stage functionalization for further derivatization.

Technology Process of [5]cycloparaphenylene

There total 4 articles about [5]cycloparaphenylene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

C30H20Br4 → [5]cycloparaphenylene (96100-94-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; for 0.25h;

DOI:10.1002/anie.201704982

Reference yield: 72.0%

C30H24O4 (1552276-82-0) → [5]cycloparaphenylene (96100-94-6)

Guidance literature:

With hydrogenchloride; tin(II) chloride dihdyrate; In tetrahydrofuran; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201406650

Reference yield: 69.0%

C32H28O2 (1582760-27-7) → [5]cycloparaphenylene (96100-94-6)

Guidance literature:

With n-butyllithium; diisopropylamine; In hexane; toluene; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1038/nchem.1888

upstream raw materials:

C₃₀H₂₄O₄

C₄₆H₅₆B₂O₈

C₃₂H₂₈O₂