Skip to main content

Molecular Wires

  • Chapter
  • First Online:
Molecular Wires and Electronics

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 257))

Abstract

Molecular wires are compounds that are proposed to be used in molecular electronic and optoelectronic devices to replace the metal and silicon-based wires in semiconductor devices. We review the field, including organic molecular wires such as oligo(2,5-thiophene ethynylene)s, oligo(1,4-phenylene ethynylene)s, oligo(1,4-phenylene vinylene)s, aromatic ladder oligomers, oligophenylenes, polyphenylenes, acetylene oligomers, carbon nanotubes, and organometallic molecular wires. We briefly review the measurement of conduction in molecular wires and conclude that fully conjugated organic aromatic molecular wires are the best candidates for introduction into new electronic devices as replacements for the Al or Cu wiring presently used in logic and memory devices.

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

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

cAFM:

conducting atomic force microscopy

CNTFETs:

carbon nanotube field effect transistors

CV:

cyclic voltammetry

DMSO:

dimethylsulfoxide

NDR:

negative differential resistance

OLED:

organic light emitting diodes

OTEs:

oligo(2-5-thiophene ethynylene)s

OPEs:

oligo(1,4-phenylene ethynylene)s

OPVs:

oligo(1,4-phenylene vinylene)s

SAM:

self-assembled monolayer

STM:

scanning tunneling microscopy

SWE:

single wavelength ellipsometry

SWNT:

single-walled nanotube

Terpy:

terpyridine

XPS:

X-ray photoelectron spectroscopy

References

  1. Tour JM (2003) Molecular electronics: commercial insights, chemistry, devices, architecture, and programming. World Scientific Publishing, River Edge, New Jersey

    Google Scholar 

  2. Tour JM, James DK (2002) Molecular electronic computing architecture. In: Goddard WA, Brenner DW, Lyshevski SE, Iafrate GJ (eds) Handbook of nanoscience, engineering, and technology. CRC Press, Boca Raton, Florida, p 4:1–4-28

    Google Scholar 

  3. Ward MD (2001) J Chem Ed 78:321

    CAS  Google Scholar 

  4. Tour JM (2000) Acc Chem Res 33:791

    CAS  Google Scholar 

  5. Heath JR (2000) Pure Appl Chem 72:11

    CAS  Google Scholar 

  6. Reed MA, Tour JM (2000) Sci Am June:68

    Google Scholar 

  7. Overton R (2000) Wired 8:242

    Google Scholar 

  8. Heath JR, Kuekes PJ, Snider GS, Williams RS (1998) Science 280:1716

    CAS  Google Scholar 

  9. James DK, Tour JM (2004) Molecular wires. In: Encyclopedia of nanoscience and nanotechnology. Marcel Dekker, New York, p 2177

    Google Scholar 

  10. Robertson N, McGowan CA (2003) Chem Soc Rev 32:96

    CAS  Google Scholar 

  11. Moore GE (1965) Electronics 38. Available on the web: ftp://download.intel.com/research/silicon/moorespaper.pdf (accessed December 2004)

  12. Mutschler AS (2004) Electronic News 13 July

    Google Scholar 

  13. Intel press release (2004) http://www.intel.com/pressroom/archive/releases/20040614corp.htm (accessed January 2005)

  14. Singer P (2004) Semiconductor International 1 December

    Google Scholar 

  15. International Technology Roadmap for Semiconductors web pages (2004) http://www.itrs.net/Common/2004Update/2004Update.htm (accessed January 2005)

  16. Wang KL (2002) J Nanosci Nanotech 2:235

    Google Scholar 

  17. Patel NK, Cinà S, Burroughes JH (2002) IEEE J Sel Topics in Quan Electronics 8:346

    CAS  Google Scholar 

  18. Popovic ZD, Aziz H (2002) IEEE J Sel Topics in Quan Electronics 8:362

    CAS  Google Scholar 

  19. Matthews SJ (2001) Laser Focus World 37:169

    CAS  Google Scholar 

  20. Cotton FA, Daniels LM, Murillo CM, Wang X (1999) Chem Commun 1999:2461

    Google Scholar 

  21. Hu J, Odom TW, Lieber CM (1999) Acc Chem Res 32:435

    CAS  Google Scholar 

  22. Chung S-W, Yu J-Y, Heath JR (2000) Appl Phys Lett 76:2068

    CAS  Google Scholar 

  23. Cui Y, Lieber CM (2001) Science 291:851

    CAS  Google Scholar 

  24. Gudiksen MS, Wang J, Lieber CM (2001) J Phys Chem B 105:4062

    CAS  Google Scholar 

  25. Reed MA, Zhou C, Muller CJ, Burgin TP, Tour JM (1997) Science 278:252

    CAS  Google Scholar 

  26. Chen J, Reed MA, Rawlett AM, Tour JM (1999) Science 286:1550

    CAS  Google Scholar 

  27. Ranganathan S, Steidel I, Anariba F, McCreery RL (2001) Nano Lett 1:491

    CAS  Google Scholar 

  28. Fan F-RF, Yang J, Cai L, Price DW, Dirk SM, Kosynkin DV, Yao Y, Rawlett AM, Tour JM, Bard AJ (2002) J Am Chem Soc 124:5550

    CAS  Google Scholar 

  29. James DK, Tour JM (2004) Chem Mater 16:4423

    CAS  Google Scholar 

  30. Bumm LA, Arnold JJ, Cygan MT, Dunbar TD, Burgin TP, Jones L, Allara DL, Tour JM, Weiss PS (1996) Science 271:1705

    CAS  Google Scholar 

  31. Pearson DL, Tour JM (1997) J Org Chem 62:1376

    CAS  Google Scholar 

  32. Pearson DL, Jones L, Schumm JS, Tour JM (1997) Synthetic Metals 84:303

    CAS  Google Scholar 

  33. Pearson DL, Jones L, Schumm JS, Tour JM (1997) Synthesis of molecular scale wires and alligator clips. In: Joachim C, Roth S (eds) Proc NATO advanced research workshop on atomic and molecular wires, Les Houches, France, 6–10 May, 1996. Applied Science Series E, Kluwer Academic Publishers, Dordrecht 341:81

    Google Scholar 

  34. Tour JM (2000) Polymer News 25:329

    CAS  Google Scholar 

  35. Jones L, Schumm JS, Tour JM (1997) J Org Chem 62:1388

    CAS  Google Scholar 

  36. Collman JP, Zhong M, Constanzo S, Sunderland CJ, Aukauloo A, Berg K, Zeng L (2001) Synthesis 2001:367

    Google Scholar 

  37. Gu T, Nierengarten J-S (2001) Tet Lett 42:3175

    CAS  Google Scholar 

  38. Tour JM, Rawlett AM, Kozaki M, Yao Y, Jagessar RC, Dirk SM, Price DW, Reed MA, Zhou C-W, Chen J, Wang W, Campbell I (2001) Chem Eur J 7:5118

    CAS  Google Scholar 

  39. Dirk SM, Price DW, Chanteau S, Kosynkin DV, Tour JM (2001) Tetrahedron 57:5109

    CAS  Google Scholar 

  40. Hwang JJ, Tour JM (2002) Tetrahedron 58:10387

    CAS  Google Scholar 

  41. Donhauser ZJ, Mantooth BA, Kelly KF, Bumm LA, Monnell JD, Stapleton JJ, Price DW, Rawlett AM, Allara DW, Tour JM, Weiss PS (2001) Science 292:2303

    CAS  Google Scholar 

  42. Chen J, Wang W, Klemic J, Reed MA, Axelrod BW, Kaschak DB, Rawlett AM, Price DW, Dirk SM, Tour JM, Grubisha DS, Bennett DW (2002) Ann N Y Acad Sci 960:69

    CAS  Google Scholar 

  43. Maya F, Flatt AK, Stewart MP, Shen DE, Tour JM (2004) Chem Mater 16:2987

    CAS  Google Scholar 

  44. Maya F, Chanteau SH, Cheng L, Stewart MP, Tour JM (2005) Chem Mater 17:1331

    CAS  Google Scholar 

  45. Flatt AK, Yao Y, Maya F, Tour JM (2004) J Org Chem 69:1752

    CAS  Google Scholar 

  46. Atienza C, Insuasty B, Seoane C, Martin N, Ramey J, Rahman GMA, Guldi DM (2005) J Mater Chem 15:124

    CAS  Google Scholar 

  47. Zhao Y, Shirai Y, Slepkov AD, Cheng L, Alemany LB, Sasaki T, Hegmann FA, Tour JM (2005) Chem Eur J 11:3643

    CAS  Google Scholar 

  48. Flatt AK, Dirk SM, Henderson JC, Shen DE, Su J, Reed MA, Tour JM (2003) Tetrahedron 59:8555

    CAS  Google Scholar 

  49. Syamakumari A, Schenning APHJ, Meijer EW (2002) Chem Eur J 8:3353

    CAS  Google Scholar 

  50. Wong MS, Li ZH, Shek MF, Samroc M, Samoc A, Luther-Davies B (2002) Chem Mater 14:2999

    CAS  Google Scholar 

  51. Gu T, Ceroni P, Marconi G, Armaroli N, Nierengarten J-F (2001) J Org Chem 66:6432

    CAS  Google Scholar 

  52. Davis WB, Ratner MA, Wasielewski MR (2001) J Am Chem Soc 123:7877

    CAS  Google Scholar 

  53. Sikes HD, Smalley JF, Dudek SP, Cook AR, Newton MD, Chidsey CE, Feldberg SW (2001) Science 291:1519

    CAS  Google Scholar 

  54. Detert H, Sugiono E (2000) Synth Metals 115:89

    CAS  Google Scholar 

  55. Tour JM, Cheng L, Nackashi DP, Yao Y, Flatt AK, St Angelo SK, Mallouk TE, Franzon PD (2003) J Am Chem Soc 125:13279

    CAS  Google Scholar 

  56. Giacalone F, Segura JL, Martin N, Guldi DM (2004) J Am Chem Soc 126:5340

    CAS  Google Scholar 

  57. Zhang CY, Tour JM (1999) J Am Chem Soc 121:8783

    CAS  Google Scholar 

  58. Yao Y, Tour JM (1999) Macromolecules 32:2455

    CAS  Google Scholar 

  59. Gourdon A (1997) Synthesis of conjugated ladder oligomers. In: Joachim C, Roth S (eds) Proc NATO advanced research workshop on atomic and molecular wires, Les Houches, France, 6–10 May, 1996. Applied Science Series E, Kluwer Academic Publishers, Dordrecht 341:81

    Google Scholar 

  60. Billić A, Reimers JR, Hush NS (2002) J Phys Chem B 106:6740

    Google Scholar 

  61. Ciszek JW, Tour JM (2004) Tetrahedron Lett 45:2801

    CAS  Google Scholar 

  62. Dameron AA, Ciszek JW, Tour JM, Weiss PS (2004) J Phys Chem B 108:16761

    CAS  Google Scholar 

  63. Tour JM (1994) Adv Mater 6:190

    CAS  Google Scholar 

  64. Tour JM, John JA (1993) Polym Prepr (Am Chem Soc Div Polym Chem) 34:372

    CAS  Google Scholar 

  65. Tour JM, Lamba JJS (1993) J Am Chem Soc 115:4935

    CAS  Google Scholar 

  66. Grimsdale AC, Müllen K (2001) The Chemical Record 1:243

    CAS  Google Scholar 

  67. Wang C, Batsanov AS, Bryce MR, Sage I (2004) Org Lett 6:2181

    CAS  Google Scholar 

  68. Maya F, Tour JM (2004) Tetrahedron 60:81

    CAS  Google Scholar 

  69. Schenning APHJ, Arndt J-D, Ito M, Stoddart A, Schrieber M, Siemsen P, Martin RE, Boudon C, Gisselbrecht JP, Gross M, Gramlich V, Diederich F (2001) Helv Chim Acta 84:296

    CAS  Google Scholar 

  70. Livingston RC, Cox LR, Gramlich V, Diederich F (2001) Angew Chem Int Ed 40:2334

    CAS  Google Scholar 

  71. Alvaro M, Ferrer B, García M, Lay A, Trinidad F, Valenciano J (2002) Chem Phys Lett 356:577

    CAS  Google Scholar 

  72. Taylor PN, O’Connell MJ, McNeill LA, Hall MJ, Aplin RT, Anderson HL (2000) Angew Chem Int Ed 39:3456

    CAS  Google Scholar 

  73. Kong J, Franklin NR, Zhou C, Chapline MC, Peng S, Cho K, Dai H (2000) Science 287:622

    CAS  Google Scholar 

  74. Franklin NR, Li Y, Chen RJ, Javey A, Dai H (2001) Appl Phys Lett 79:4571

    CAS  Google Scholar 

  75. Bahr JL, Mickelson ET, Bronikowski MJ, Smalley RE, Tour JM (2001) Chem Commun 2001:193

    Google Scholar 

  76. Bahr JL, Tour JM (2002) J Mater Chem 12:1952

    CAS  Google Scholar 

  77. Bahr JL, Tour JM (2001) Chem Mater 13:3823

    CAS  Google Scholar 

  78. Dyke CA, Tour JM (2004) Chem Eur J 10:812

    CAS  Google Scholar 

  79. Hudson JL, Casavant MJ, Tour JM (2004) J Am Chem Soc 126:11158

    CAS  Google Scholar 

  80. Seifert G, Köhler T, Frauenheim T (2000) Appl Phys Lett 77:1313

    CAS  Google Scholar 

  81. Ciszek J, Tour JM Unpublished results

    Google Scholar 

  82. Yu LH, Keane ZK, Ciszek JW, Cheng L, Stewart MP, Tour JM, Natelson D (2004) Phys Rev Lett 92:266802

    Google Scholar 

  83. Ambroise A, Kirmaier C, Wagner RW, Loewe RS, Bocian DF, Holten D, Lindsey JS (2002) J Org Chem 76:3811 and references cited therein

    Google Scholar 

  84. Anderson HLB (1999) Chem Commun 1999:2323

    Google Scholar 

  85. Iengo E, Zangrando E, Minatel R, Alessio E (2002) J Am Chem Soc 124:1003

    CAS  Google Scholar 

  86. Kimizuku N (2000) Adv Mater 12:1461

    Google Scholar 

  87. Constable EC, Housecroft CE, Schofield ER, Encinas S, Armaroli N, Barigelletti F, Flamigni L, Figgemeier E, Vos JG (1999) Chem Commun 1999:869

    Google Scholar 

  88. Shiotsuka M, Yamamoto Y, Okuno S, Kitou M, Nozaki K, Onaka S (2002) Chem Commun 2002:590

    Google Scholar 

  89. Berry JF, Cotton FA, Daniels LM, Murillo CA (2002) J Am Chem Soc 124:3212

    CAS  Google Scholar 

  90. Barigelletti F, Flamigini L (2000) Chem Soc Rev 29:1

    CAS  Google Scholar 

  91. Dong T-Y, Lin M-C, Chiang MY-N, Wu J-Y (2004) Organometallics 23:3921

    CAS  Google Scholar 

  92. Fraysse S, Coudret C, Launay J-P (2003) J Am Chem Soc 125:5880

    CAS  Google Scholar 

  93. Hortholary C, Coudret C (2003) J Org Chem 68:2167

    CAS  Google Scholar 

  94. Berry JF, Cotton FA, Murillo CA (2003) Dalton Trans 2003:3015

    Google Scholar 

  95. Berry JF, Cotton FA, Lu T, Murillo CA, Wang X (2003) Inorg Chem 42:3595

    CAS  Google Scholar 

  96. Berry JF, Cotton FA, Murillo CA, Roberts BK (2004) Inorg Chem 43:2277

    CAS  Google Scholar 

  97. Hartl F, Mahabiersing T, Chardon-Noblat S, Da Costa P, Deronzier A (2004) Inorg Chem 43:7250

    CAS  Google Scholar 

  98. Stang SL, Paul F, Lapinte C (2000) Organometallics 19:1035

    Google Scholar 

  99. Lehmann J, Kohler S, Hänggi P, Nitzan A (2002) Phys Rev Lett 88:228305-1

    Google Scholar 

  100. Weber HB, Reichert J, Weigend F, Ochs R, Beckmann D, Mayer M, Ahlrichs R, Löhneysen H (2002) Chem Phys 281:113

    CAS  Google Scholar 

  101. Chen J, Reed MA (2002) Chem Phys 281:127

    CAS  Google Scholar 

  102. Agraït N, Untiedt C, Rubio-Bollinger G, Vieira S (2002) Chem Phys 281:231

    Google Scholar 

  103. Patrone L, Palacin S, Bourgoin JP, Laboute J, Zambelli T, Gauthier S (2002) Chem Phys 281:325

    CAS  Google Scholar 

  104. Davis WB, Ratner MA, Wasielewski MR (2002) Chem Phys 281:333

    CAS  Google Scholar 

  105. Rampi MA, Whitesides GM (2002) Chem Phys 281:373

    CAS  Google Scholar 

  106. Avouris P (2002) Chem Phys 281:429-445

    CAS  Google Scholar 

  107. Cuniberti G, Fagas G, Richter K (2002) Chem Phys 281:465

    CAS  Google Scholar 

  108. Kushmerick JG, Holt DB, Pollack SK, Ratner MA, Yang JC, Schull TL, Naciri J, Moore MH, Shashidhar R (2002) J Am Chem Soc 124:10654

    CAS  Google Scholar 

  109. Rawlett AM, Hopson TJ, Nagahara LA, Tsui RK, Ramachandran GK, Lindsay SM (2002) Appl Phys Lett 81:3043

    CAS  Google Scholar 

  110. Lee T, Wang W, Reed MA (2003) Ann NY Acad Sci 21

    Google Scholar 

  111. Kushmerick JG, Naciri J, Yang JC, Shashidar R (2003) Nano Lett 3:897

    CAS  Google Scholar 

  112. Blum AS, Kushmerick JG, Pollack SK, Yang JC, Moore M, Naciri J, Shashidar R, Ratna BR (2004) J Phys Chem B 108:18124

    CAS  Google Scholar 

  113. Blum AS, Yang JC, Shashidar R, Ratna B (2003) Appl Phys Lett 82:3322

    CAS  Google Scholar 

  114. Dholakia GR, Fan W, Koehne J, Han J, Meyyappan M (2004) Phys Chem Rev B 69:153402

    Google Scholar 

  115. Ishida T, Mizutani W, Liang T-T, Azehara H, Miyake K, Sasaki S, Tokumoto H (2003) Ann NY Acad Sci 1006:164

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dustin K. James .

Rights and permissions

Reprints and permissions

Copyright information

© 2005 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

James, D.K., Tour, J.M. (2005). Molecular Wires. In: Molecular Wires and Electronics. Topics in Current Chemistry, vol 257. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136066

Download citation

Publish with us

Policies and ethics