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.
Preview
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
Tour JM (2003) Molecular electronics: commercial insights, chemistry, devices, architecture, and programming. World Scientific Publishing, River Edge, New Jersey
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
Ward MD (2001) J Chem Ed 78:321
Tour JM (2000) Acc Chem Res 33:791
Heath JR (2000) Pure Appl Chem 72:11
Reed MA, Tour JM (2000) Sci Am June:68
Overton R (2000) Wired 8:242
Heath JR, Kuekes PJ, Snider GS, Williams RS (1998) Science 280:1716
James DK, Tour JM (2004) Molecular wires. In: Encyclopedia of nanoscience and nanotechnology. Marcel Dekker, New York, p 2177
Robertson N, McGowan CA (2003) Chem Soc Rev 32:96
Moore GE (1965) Electronics 38. Available on the web: ftp://download.intel.com/research/silicon/moorespaper.pdf (accessed December 2004)
Mutschler AS (2004) Electronic News 13 July
Intel press release (2004) http://www.intel.com/pressroom/archive/releases/20040614corp.htm (accessed January 2005)
Singer P (2004) Semiconductor International 1 December
International Technology Roadmap for Semiconductors web pages (2004) http://www.itrs.net/Common/2004Update/2004Update.htm (accessed January 2005)
Wang KL (2002) J Nanosci Nanotech 2:235
Patel NK, Cinà S, Burroughes JH (2002) IEEE J Sel Topics in Quan Electronics 8:346
Popovic ZD, Aziz H (2002) IEEE J Sel Topics in Quan Electronics 8:362
Matthews SJ (2001) Laser Focus World 37:169
Cotton FA, Daniels LM, Murillo CM, Wang X (1999) Chem Commun 1999:2461
Hu J, Odom TW, Lieber CM (1999) Acc Chem Res 32:435
Chung S-W, Yu J-Y, Heath JR (2000) Appl Phys Lett 76:2068
Cui Y, Lieber CM (2001) Science 291:851
Gudiksen MS, Wang J, Lieber CM (2001) J Phys Chem B 105:4062
Reed MA, Zhou C, Muller CJ, Burgin TP, Tour JM (1997) Science 278:252
Chen J, Reed MA, Rawlett AM, Tour JM (1999) Science 286:1550
Ranganathan S, Steidel I, Anariba F, McCreery RL (2001) Nano Lett 1:491
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
James DK, Tour JM (2004) Chem Mater 16:4423
Bumm LA, Arnold JJ, Cygan MT, Dunbar TD, Burgin TP, Jones L, Allara DL, Tour JM, Weiss PS (1996) Science 271:1705
Pearson DL, Tour JM (1997) J Org Chem 62:1376
Pearson DL, Jones L, Schumm JS, Tour JM (1997) Synthetic Metals 84:303
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
Tour JM (2000) Polymer News 25:329
Jones L, Schumm JS, Tour JM (1997) J Org Chem 62:1388
Collman JP, Zhong M, Constanzo S, Sunderland CJ, Aukauloo A, Berg K, Zeng L (2001) Synthesis 2001:367
Gu T, Nierengarten J-S (2001) Tet Lett 42:3175
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
Dirk SM, Price DW, Chanteau S, Kosynkin DV, Tour JM (2001) Tetrahedron 57:5109
Hwang JJ, Tour JM (2002) Tetrahedron 58:10387
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
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
Maya F, Flatt AK, Stewart MP, Shen DE, Tour JM (2004) Chem Mater 16:2987
Maya F, Chanteau SH, Cheng L, Stewart MP, Tour JM (2005) Chem Mater 17:1331
Flatt AK, Yao Y, Maya F, Tour JM (2004) J Org Chem 69:1752
Atienza C, Insuasty B, Seoane C, Martin N, Ramey J, Rahman GMA, Guldi DM (2005) J Mater Chem 15:124
Zhao Y, Shirai Y, Slepkov AD, Cheng L, Alemany LB, Sasaki T, Hegmann FA, Tour JM (2005) Chem Eur J 11:3643
Flatt AK, Dirk SM, Henderson JC, Shen DE, Su J, Reed MA, Tour JM (2003) Tetrahedron 59:8555
Syamakumari A, Schenning APHJ, Meijer EW (2002) Chem Eur J 8:3353
Wong MS, Li ZH, Shek MF, Samroc M, Samoc A, Luther-Davies B (2002) Chem Mater 14:2999
Gu T, Ceroni P, Marconi G, Armaroli N, Nierengarten J-F (2001) J Org Chem 66:6432
Davis WB, Ratner MA, Wasielewski MR (2001) J Am Chem Soc 123:7877
Sikes HD, Smalley JF, Dudek SP, Cook AR, Newton MD, Chidsey CE, Feldberg SW (2001) Science 291:1519
Detert H, Sugiono E (2000) Synth Metals 115:89
Tour JM, Cheng L, Nackashi DP, Yao Y, Flatt AK, St Angelo SK, Mallouk TE, Franzon PD (2003) J Am Chem Soc 125:13279
Giacalone F, Segura JL, Martin N, Guldi DM (2004) J Am Chem Soc 126:5340
Zhang CY, Tour JM (1999) J Am Chem Soc 121:8783
Yao Y, Tour JM (1999) Macromolecules 32:2455
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
Billić A, Reimers JR, Hush NS (2002) J Phys Chem B 106:6740
Ciszek JW, Tour JM (2004) Tetrahedron Lett 45:2801
Dameron AA, Ciszek JW, Tour JM, Weiss PS (2004) J Phys Chem B 108:16761
Tour JM (1994) Adv Mater 6:190
Tour JM, John JA (1993) Polym Prepr (Am Chem Soc Div Polym Chem) 34:372
Tour JM, Lamba JJS (1993) J Am Chem Soc 115:4935
Grimsdale AC, Müllen K (2001) The Chemical Record 1:243
Wang C, Batsanov AS, Bryce MR, Sage I (2004) Org Lett 6:2181
Maya F, Tour JM (2004) Tetrahedron 60:81
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
Livingston RC, Cox LR, Gramlich V, Diederich F (2001) Angew Chem Int Ed 40:2334
Alvaro M, Ferrer B, GarcÃa M, Lay A, Trinidad F, Valenciano J (2002) Chem Phys Lett 356:577
Taylor PN, O’Connell MJ, McNeill LA, Hall MJ, Aplin RT, Anderson HL (2000) Angew Chem Int Ed 39:3456
Kong J, Franklin NR, Zhou C, Chapline MC, Peng S, Cho K, Dai H (2000) Science 287:622
Franklin NR, Li Y, Chen RJ, Javey A, Dai H (2001) Appl Phys Lett 79:4571
Bahr JL, Mickelson ET, Bronikowski MJ, Smalley RE, Tour JM (2001) Chem Commun 2001:193
Bahr JL, Tour JM (2002) J Mater Chem 12:1952
Bahr JL, Tour JM (2001) Chem Mater 13:3823
Dyke CA, Tour JM (2004) Chem Eur J 10:812
Hudson JL, Casavant MJ, Tour JM (2004) J Am Chem Soc 126:11158
Seifert G, Köhler T, Frauenheim T (2000) Appl Phys Lett 77:1313
Ciszek J, Tour JM Unpublished results
Yu LH, Keane ZK, Ciszek JW, Cheng L, Stewart MP, Tour JM, Natelson D (2004) Phys Rev Lett 92:266802
Ambroise A, Kirmaier C, Wagner RW, Loewe RS, Bocian DF, Holten D, Lindsey JS (2002) J Org Chem 76:3811 and references cited therein
Anderson HLB (1999) Chem Commun 1999:2323
Iengo E, Zangrando E, Minatel R, Alessio E (2002) J Am Chem Soc 124:1003
Kimizuku N (2000) Adv Mater 12:1461
Constable EC, Housecroft CE, Schofield ER, Encinas S, Armaroli N, Barigelletti F, Flamigni L, Figgemeier E, Vos JG (1999) Chem Commun 1999:869
Shiotsuka M, Yamamoto Y, Okuno S, Kitou M, Nozaki K, Onaka S (2002) Chem Commun 2002:590
Berry JF, Cotton FA, Daniels LM, Murillo CA (2002) J Am Chem Soc 124:3212
Barigelletti F, Flamigini L (2000) Chem Soc Rev 29:1
Dong T-Y, Lin M-C, Chiang MY-N, Wu J-Y (2004) Organometallics 23:3921
Fraysse S, Coudret C, Launay J-P (2003) J Am Chem Soc 125:5880
Hortholary C, Coudret C (2003) J Org Chem 68:2167
Berry JF, Cotton FA, Murillo CA (2003) Dalton Trans 2003:3015
Berry JF, Cotton FA, Lu T, Murillo CA, Wang X (2003) Inorg Chem 42:3595
Berry JF, Cotton FA, Murillo CA, Roberts BK (2004) Inorg Chem 43:2277
Hartl F, Mahabiersing T, Chardon-Noblat S, Da Costa P, Deronzier A (2004) Inorg Chem 43:7250
Stang SL, Paul F, Lapinte C (2000) Organometallics 19:1035
Lehmann J, Kohler S, Hänggi P, Nitzan A (2002) Phys Rev Lett 88:228305-1
Weber HB, Reichert J, Weigend F, Ochs R, Beckmann D, Mayer M, Ahlrichs R, Löhneysen H (2002) Chem Phys 281:113
Chen J, Reed MA (2002) Chem Phys 281:127
Agraït N, Untiedt C, Rubio-Bollinger G, Vieira S (2002) Chem Phys 281:231
Patrone L, Palacin S, Bourgoin JP, Laboute J, Zambelli T, Gauthier S (2002) Chem Phys 281:325
Davis WB, Ratner MA, Wasielewski MR (2002) Chem Phys 281:333
Rampi MA, Whitesides GM (2002) Chem Phys 281:373
Avouris P (2002) Chem Phys 281:429-445
Cuniberti G, Fagas G, Richter K (2002) Chem Phys 281:465
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
Rawlett AM, Hopson TJ, Nagahara LA, Tsui RK, Ramachandran GK, Lindsay SM (2002) Appl Phys Lett 81:3043
Lee T, Wang W, Reed MA (2003) Ann NY Acad Sci 21
Kushmerick JG, Naciri J, Yang JC, Shashidar R (2003) Nano Lett 3:897
Blum AS, Kushmerick JG, Pollack SK, Yang JC, Moore M, Naciri J, Shashidar R, Ratna BR (2004) J Phys Chem B 108:18124
Blum AS, Yang JC, Shashidar R, Ratna B (2003) Appl Phys Lett 82:3322
Dholakia GR, Fan W, Koehne J, Han J, Meyyappan M (2004) Phys Chem Rev B 69:153402
Ishida T, Mizutani W, Liang T-T, Azehara H, Miyake K, Sasaki S, Tokumoto H (2003) Ann NY Acad Sci 1006:164
Author information
Authors and Affiliations
Corresponding author
Rights 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
DOI: https://doi.org/10.1007/b136066
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-25793-6
Online ISBN: 978-3-540-31459-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)