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Cyclobis(paraquat-p-phenylene)

Cyclobis(paraquat-p-phenylene)
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C36H32N4/c1-2-30-4-3-29(1)25-37-17-9-33(10-18-37)35-13-21-39(22-14-35)27-31-5-7-32(8-6-31)28-40-23-15-36(16-24-40)34-11-19-38(26-30)20-12-34/h1-24H,25-28H2/q+4
    Key: URORLZXVTFVIPS-UHFFFAOYSA-N
  • InChI=1/C36H32N4/c1-2-30-4-3-29(1)25-37-17-9-33(10-18-37)35-13-21-39(22-14-35)27-31-5-7-32(8-6-31)28-40-23-15-36(16-24-40)34-11-19-38(26-30)20-12-34/h1-24H,25-28H2/q+4
    Key: URORLZXVTFVIPS-UHFFFAOYAV
  • c1cc2ccc1C[n+]3ccc(cc3)-c4cc[n+](cc4)Cc5ccc(cc5)C[n+]6ccc(cc6)-c7cc[n+](cc7)C2
Properties
C36H32N4
Molar mass 520.663 g·mol−1
Appearance white solid [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclobis(paraquat-p-phenylene) (formally a derivative of paraquat) belongs to the class of cyclophanes, and consists of aromatic units connected by methylene bridges. It is able to incorporate small guest molecule and has played an important role in host–guest chemistry and supramolecular chemistry.[2]

The cyclophane is also referred to as Stoddart's blue box because its inventor, J. Fraser Stoddart, illustrates the electron-poor areas of molecules in a blue shade.[3]

  1. ^ Masumi Asakawa; Wim Dehaen; Gerrit L’abbé; Stephan Menzer; Jan Nouwen; Françisco M. Raymo; J. Fraser Stoddart; David J. Williams (January 1996), "Improved Template-Directed Synthesis of Cyclobis(paraquat-phenylene)", The Journal of Organic Chemistry, vol. 61, no. 26, pp. 9591–9595, doi:10.1021/jo961488i, ISSN 0022-3263
  2. ^ Jonathan C. Barnes; Michal Juríček; Nicolaas A. Vermeulen; Edward J. Dale; J. Fraser Stoddart (2013), "Synthesis of ExnBox Cyclophanes", The Journal of Organic Chemistry, vol. 78, no. 23, pp. 11962–11969, doi:10.1021/jo401993n, PMID 24128112
  3. ^ Atwood, Jerry L.; Steed, Jonathan W. (2013). Supramolecular chemistry. Hoboken, N.J.: Wiley. ISBN 978-1-118-68150-3.

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