Skip to main content
SpringerLink
Log in
Book cover

The Power of Click Chemistry for Molecular Machines and Surface Patterning pp 83–100Cite as

A Push-Button Molecular Switch

  • Chapter
  • First Online:

  • 695 Accesses

Part of the book series: Springer Theses ((Springer Theses))

Abstract

The preparation, characterization, and switching mechanism of a unique single-station mechanically switchable hetero[2]catenane are reported. The facile synthesis utilizing a “threading-followed-by-clipping” protocol features the Cu2+-catalyzed Eglinton coupling as a mild and efficient route to the tetrathiafulvalene-based catenane in high yield. The resulting mechanically interlocked molecule operates as a perfect molecular switch, most readily described as a “push-button,” whereby two discrete and fully occupied translational states are toggled electrochemically at incredibly fast rates. This mechanical switching is probed using a wide variety of experimental techniques as well as by quantum mechanical investigations. The fundamental distinctions between this single-station [2]catenane and other more traditional bi- and multistation molecular switches are significant.

This Chapter is reproduced in part with permission from: Spruell JM, Paxton WF, Olsen J-C, Benítez D, Tkatchouk E, Stern CL, Trabolsi A, Friedman DC, Goddard WA, Stoddart JF, J. Am. Chem. Soc.2009, 131, 11571–11580.

Author Contributions: J.M. Spruell and W.F. Paxton conceived the project. J.M. Spruell and J.F. Stoddart prepared the original manuscript. J.M. Spruell synthesized all compounds investigated in this work. D. Benítez, E. Tkatchouk and W.A. Goddard performed DFT calculations. J.M. Spruell and D.C. Friedman performed NMR spectroscopic investigations together. J.M. Spruell and A. Trabolsi performed electrochemical analysis together.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  1. Collin J-P, Heitz V, Sauvage J-P (2005) Top Curr Chem 262:29–62

    Article  CAS  Google Scholar 

  2. Schalley CA, Weilandt T, Brüggemann J, Vögtle F (2004) Top Curr Chem 248:141–200

    Google Scholar 

  3. Godt A (2004) Eur J Org Chem, pp 1639–1654

    Google Scholar 

  4. Lankshear MD, Beer PD (2007) Acc Chem Res 40:657–668

    Article  CAS  Google Scholar 

  5. Dichtel WR, Miljanić OŠ, Zhang W, Spruell JM, Patel K, Aprahamian I, Heath JR, Stoddart JF (2008) Acc Chem Res 41:1750–1761

    Article  CAS  Google Scholar 

  6. Fujita M (1999) Acc Chem Res 32:53–61

    Article  CAS  Google Scholar 

  7. Anderson S, Anderson HL, Sanders JKM (1993) Acc Chem Res 26:469–475

    Article  CAS  Google Scholar 

  8. Cacciapaglia R, Mandolini L (1993) Chem Soc Rev 22:221–231

    Article  CAS  Google Scholar 

  9. Schneider JP, Kelly JW (1995) Chem Rev 95:2169–2187

    Article  CAS  Google Scholar 

  10. Stoddart JF, Tseng H-R (2002) Proc Natl Acad Sci USA 99:4797–4800

    Article  CAS  Google Scholar 

  11. Aricó F, Badjić JD, Cantrill SJ, Flood AH, Leung KC-F, Liu Y, Stoddart JF (2005) Top Curr Chem 249:203–259

    Google Scholar 

  12. Williams AR, Northrop BH, Chang T, Stoddart JF, White AJP, Williams DJ (2006) Angew Chem Int Ed 45:6665–6669

    Article  CAS  Google Scholar 

  13. Northrop BH, Aricó F, Tangchiavang N, Badjić JD, Stoddart JF (2006) Org Lett 8:3899–3902

    Article  CAS  Google Scholar 

  14. Cantrill SJ, Poulin-Kerstein KG, Grubbs RH, Lanari D, Leung KC-F, Nelson A, Smidt SP, Stoddart JF, Tirrell DA (2005) Org Lett 7:4213–4216

    Article  CAS  Google Scholar 

  15. Philp D, Stoddart JF (1991) Synlett 445–458

    Google Scholar 

  16. Philp D, Stoddart JF (1996) Angew Chem Int Ed 35:1155–1196

    CAS  Google Scholar 

  17. Kay ER, Leigh DA, Zerbetto F (2007) Angew Chem Int Ed 46:72–191

    Article  CAS  Google Scholar 

  18. Saha S, Stoddart JF (2007) Chem Soc Rev 36:77–92

    Article  CAS  Google Scholar 

  19. Green JE, Choi JW, Boukai A, Bunimovich Y, Johnston-Halpering E, DeIonno E, Luo Y, Sheriff BA, Xu K, Shin YS, Tseng H-R, Stoddart JF, Heath JR (2007) Nature 445:414–417

    Article  CAS  Google Scholar 

  20. Tseng H-R, Wu DM, Fang NXL, Zhang X, Stoddart JF (2004) Chem Phys Chem 5:111–116

    CAS  Google Scholar 

  21. Luo Y, Collier CP, Jeppesen JO, Nielsen KA, DeIonno E, Ho G, Perkins J, Tseng H-R, Yamamoto T, Stoddart JF, Heath JR (2002) Chem Phys Chem 3:519–525

    CAS  Google Scholar 

  22. Dichtel WR, Heath JR, Stoddart JF (2007) Philos Trans R Soc London Ser A 365:1607–1625

    Article  CAS  Google Scholar 

  23. Flood AH, Stoddart JF, Steuerman DW, Heath JR (2004) Science 306:2055–2056

    Article  CAS  Google Scholar 

  24. Viterisi A, Orsini A, Weibel JM, Pale P (2006) Tetrahedron Lett 47:2779–2781

    Article  CAS  Google Scholar 

  25. Liu Y, Flood AH, Bonvallett PA, Vignon SA, Northrop BH, Tseng H-R, Jeppesen JO, Huang TJ, Brough B, Baller M, Magonov S, Solares SD, Goddard WA, Ho CM, Stoddart JF (2005) J Am Chem Soc 127:9745–9759

    Article  CAS  Google Scholar 

  26. Steuerman DW, Tseng H-R, Peters AJ, Flood AH, Jeppesen JO, Nielsen KA, Stoddart JF, Heath JR (2004) Angew Chem Int Ed 43:6486–6491

    Article  CAS  Google Scholar 

  27. Tseng H-R, Vignon SA, Celestre PC, Perkins J, Jeppesen JO, Di Fabio A, Ballardini R, Gandolfi MT, Venturi M, Balzani V, Stoddart JF (2004) Chem Eur J 10:155–172

    Article  CAS  Google Scholar 

  28. Leigh DA, Wong JKY, Dehez F, Zerbetto F (2003) Nature 424:174–179

    Article  CAS  Google Scholar 

  29. Balzani V, Credi A, Ferrer B, Silvi S, Venturi M (2005) Top Curr Chem 262:1–27

    Article  CAS  Google Scholar 

  30. Mandl CP, König B (2004) Angew Chem Int Ed 43:1622–1624

    Article  CAS  Google Scholar 

  31. Hernández JV, Kay ER, Leigh DA (2004) Science 306:1532–1537

    Article  Google Scholar 

  32. Flood AH, Peters AJ, Vignon SA, Steuerman DW, Tseng H-R, Kang S, Heath JR, Stoddart JF (2004) Chem Eur J 10:6558–6564

    Article  CAS  Google Scholar 

  33. Asakawa M, Dehaen W, L’abbé G, Menzer S, Nouwen J, Raymo FM, Stoddart JF, Williams DJ (1996) J Org Chem 61:9591–9595

    Article  CAS  Google Scholar 

  34. Doddi G, Ercolani G, Mencarelli P, Piermattei A (2005) J Org Chem 70:3761–3764

    Article  CAS  Google Scholar 

  35. Odell B, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1988) Angew Chem Int Ed Engl 27:1547–1550

    Article  Google Scholar 

  36. Asakawa M, Ashton PR, Balzani V, Credi A, Hamers C, Matterstig G, Montalti M, Shipway AN, Spencer N, Stoddart JF, Tolley MS, Venturi M, White AJP, Williams DJ (1998) Angew Chem Int Ed 37:333–337

    Article  CAS  Google Scholar 

  37. Ashton PR, Goodnow TT, Kaifer AE, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Vicent C, Williams DJ (1989) Angew Chem Int Ed Engl 28:1396–1399

    Article  Google Scholar 

  38. Anelli P-L, Spencer N, Stoddart JF (1991) J Am Chem Soc 113:5131–5133

    Article  CAS  Google Scholar 

  39. Dichtel WR, Miljanić OŠ, Spruell JM, Heath JR, Stoddart JF (2006) J Am Chem Soc 128:10388–10390

    Article  CAS  Google Scholar 

  40. Miljanić OŠ, Dichtel WR, Mortezaei S, Stoddart JF (2006) Org Lett 8:4835–4838

    Article  Google Scholar 

  41. Miljanić OŠ, Dichtel WR, Khan SI, Mortezaei S, Heath JR, Stoddart JF (2007) J Am Chem Soc 129:8236–8246

    Article  Google Scholar 

  42. Spruell JM, Dichtel WR, Heath JR, Stoddart JF (2008) Chem Eur J 14:1468–1477

    Article  Google Scholar 

  43. Braunschweig AB, Dichtel WR, Miljanić OŠ, Olson MA, Spruell JM, Khan SI, Heath JR, Stoddart JF (2007) Chem Asian J 2:634–647

    Article  CAS  Google Scholar 

  44. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596–2599

    Article  CAS  Google Scholar 

  45. Siemsen P, Livingston RC, Diederich F (2000) Angew Chem Int Ed 39:2633–2657

    Article  Google Scholar 

  46. Kim HC, Chun K (2007) IEEJ Trans 2:249–261

    CAS  Google Scholar 

  47. Duda S, Godt A (2003) Eur J Org Chem, pp 3412–3420

    Google Scholar 

  48. Ünsal Ö, Godt A (1999) Chem Eur J 5:1728–1733

    Article  Google Scholar 

  49. Hamilton DG, Sanders JKM, Davies JE, Clégg W, Teat SJ (1997) Chem Commun pp 897–898

    Google Scholar 

  50. Hamilton DG, Feeder N, Prodi L, Teat SJ, Clegg W, Sanders JKM (1998) J Am Chem Soc 120:1096–1097

    Article  CAS  Google Scholar 

  51. Hamilton DG, Prodi L, Feeder N, Sanders JKM (1999) J Chem Soc Perkin Trans 1:1057–1065

    Article  Google Scholar 

  52. Dietrich-Buchecker CO, Hemmert C, Khémiss A-K, Sauvage J-P (1990) J Am Chem Soc 112:8002–8008

    Article  CAS  Google Scholar 

  53. Dietrich-Buchecker CO, Khémiss A, Sauvage J-P (1986) J Chem Soc Chem Commun 1376–1378

    Google Scholar 

  54. Gunter MJ, Farquhar SM (2003) Org Biomol Chem 1:3450–3457

    Article  CAS  Google Scholar 

  55. Sato Y, Yamasaki R, Saito S (2009) Angew Chem Int Ed 48:504–507

    Article  CAS  Google Scholar 

  56. Vignon SA, Stoddart JF (2005) Collect Czech Chem Commun 70:1493–1576

    Article  CAS  Google Scholar 

  57. Souizi A, Robert A (1987) J Org Chem 52:1610–1611

    Article  CAS  Google Scholar 

  58. Tseng H-R, Vignon SA, Stoddart JF (2003) Angew Chem Int Ed 42:1491–1495

    Article  CAS  Google Scholar 

  59. Connelly NG, Geiger WE (1996) Chem Rev 96:877–910

    Article  CAS  Google Scholar 

  60. Babaei A, Connor PA, McQuillan AJ, Umapathy S (1997) J Chem Educ 74:1200–1204

    Article  CAS  Google Scholar 

  61. Zhao Y, Truhlar DG (2008) Theo Chem Acc 120:215–241

    Article  CAS  Google Scholar 

  62. Zhao Y, Truhlar DG (2008) Acc Chem Res 41:157–167

    Article  CAS  Google Scholar 

  63. Benítez D, Tkatchouk E, Yoon I, Stoddart JF, Goddard WA III (2008) J Am Chem Soc 130:14928–14929

    Article  Google Scholar 

  64. Fuchter MJ, Beall LS, Baum SM, Montalban AG, Sakellariou EG, Mani NS, Miller T, Vesper BJ, White AJP, Williams DJ, Barrett AGM, Hoffman BM (2005) Tetrahedron 46:6115–6130

    Article  Google Scholar 

  65. Andreu R, Garín J, Orduna J, Savirón M, Cousseau J, Gorgues A, Morisson V, Nozdryn T, Becher J, Clausen RP, Bryce MR, Skabara PJ, Dehaen W (1994) Tetrahedron Lett 35:9243–9246

    Article  CAS  Google Scholar 

  66. Gottlieb HG, Kotlyar V, Nudelman A (1997) J Org Chem 62:7512–7515

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute and Materials Research Laboratory, University of California, Santa Barbara, CA, USA

    Jason M. Spruell

Authors
  1. Jason M. Spruell
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jason M. Spruell .

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer Science+Business Media, LLC

About this chapter

Cite this chapter

Spruell, J.M. (2011). A Push-Button Molecular Switch. In: The Power of Click Chemistry for Molecular Machines and Surface Patterning. Springer Theses. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-9647-3_6

Download citation

Publish with us

Policies and ethics

Search

Navigation