Abstract
This chapter focused on the synthesis and fundamental properties of π-stacked polymers, which consist of the stacked π-electron systems created by the [m.n]cyclophane, in particular [2.2]paracyclophane, in the polymer main chain. Our recent works in this field are mainly focused on due to the limited examples, and their characteristic features are summarized. Incorporation of the [2.2]paracyclophane skeleton into a π-conjugated polymer backbone leads to a π-stacked structure. Pseudo-para-, pseudo-ortho-, and pseudo-geminal-disubstituted [2.2]paracyclophanes allow the construction of various π-stacked conformations such as straight, zigzag, and fully stacked structures. Optically active π-stacked polymers comprising the planar chiral pseudo-ortho-disubstituted [2.2]paracyclophanes open a new frontier in chiral polymer chemistry. Common π-conjugated polymers have a set of HOMO (valence band) and LUMO (conduction band) energy bandgaps, whereas in the π-stacked polymers each π-electron system has its own HOMO–LUMO energy bandgap. Various aromatic groups can be incorporated into polymers; therefore, energy and charge transfer through the polymer chain can be controlled by appropriate tuning of the bandgaps and energy levels of the stacked π-electron system. We hope that this new class of π-stacked polymers can make a fundamental contribution to the field of molecular electronics in the form of single molecular wires.
Keywords
- High Occupied Molecular Orbital
- Lower Unoccupied Molecular Orbital
- Fluorescence Resonance Energy Transfer
- Photoluminescence Spectrum
- Polymer Main Chain
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Brown CJ, Farthing AC (1949) Nature 164:915
Cram DJ, Steinberg H (1951) J Am Chem Soc 73:5691
Vögtle F (1993) Cyclophane chemistry: synthesis, structures and reactions. Wiley, Chichester
Gleiter R, Hopf H (eds) (2004) Modern cyclophane chemistry. Wiley-VCH, Weinheim
Morisaki Y, Chujo Y (2006) Angew Chem Int Ed 45:6430
Morisaki Y, Chujo Y (2008) Prog Polym Sci 33:346
Hopf H (2008) Angew Chem Int Ed 47:9808
Morisaki Y, Chujo Y (2008) Bull Chem Soc Jpn 82:1070
Morisaki Y, Chujo Y (2011) Polym Chem 2:1249
Morisaki Y, Chujo Y (2012) Chem Lett 41:840
Mizogami S, Yoshimura S (1985) J Chem Soc Chem Commun 427
Mizogami S, Yoshimura S (1985) J Chem Soc Chem Commun 1736
Guyard L, Audebert P (2001) Electrochem Commun 3:164
Guyard L, Audebert P, Dolbier WR Jr, Duan JX (2002) J Electroanal Chem 537:189
Salhi F, Lee B, Metz C, Bottomley LA, Collard DM (2002) Org Lett 4:3195
Salhi F, Collard DM (2003) Adv Mater 15:81
Diederich F, Stang PJ (eds) (1998) Metal-catalyzed cross-coupling reactions. VCH, Weinheim
Miyaura N (ed) (2002) Cross-coupling reaction: a practical guide. Springer, Berlin
Negishi E (ed) (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley, New York
de Meijere A, Diedrich F (eds) (2004) Metal-catalyzed cross-coupling reactions. Wiely-VCH, Weinheim
Tohda Y, Sonogashira K, Hagihara N (1977) Synthesis 777
Sonogashira K (2002) In: Negishi E (ed) Handbook of organopalladium chemistry for organic synthesis. Wiley, New York, pp 493–529
Morisaki Y, Chujo Y (2002) Macromolecules 35:587
Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581
Heck RF, Nolley JP Jr (1972) J Org Chem 37:2320
Morisaki Y, Chujo Y (2004) Macromolecules 37:4099
Miyaura N, Yamada K, Suzuki A (1979) Tetrahedron Lett 20:3437
Miyaura N, Suzuki A (1995) Chem Rev 95:2457
Morisaki Y, Chujo Y (2005) Bull Chem Soc Jpn 78:288
Morisaki Y, Ueno S, Saeki A, Asano A, Seki S, Chujo Y (2012) Chem Eur J 18:4216
Bubeck C (1998) In: Müllen K, Wegner G (eds) Electronic materials: the oligomer approach, Wiley-VCH, Weinheim pp 449–478
Meier H, Stalmach U, Kolshorn H (1997) Acta Polym 48:379
Luo Y, Norman P, Ruud K, Agren H (1998) Chem Phys Lett 285:160
Dembinski R, Bartik T, Bartik B, Jaeger M, Gladysz JA (2000) J Am Chem Soc 122:810
Gibtner T, Hampel F, Gisselbrecht JP, Hirsch A (2002) Chem Eur J 8:408–432
Meier H (2006) Carbon-rich compounds. In: Haley MM, Tykwinski RR (eds) Molecules to materials. Wiely-VCH, Weinheim, pp 476–528
Nakano T (2010) Polym J 42:103
Nakano T, Takewaki K, Yade T, Okamoto Y (2001) J Am Chem Soc 123:9182
Nakano T, Yade T (2003) J Am Chem Soc 125:15474
Nakano T, Yade T, Yokoyama M, Nagayama N (2004) Chem Lett 33:296
Nakano T, Yade T, Fukuda Y, Yamaguchi T, Okumura S (2005) Macromolecules 38:8140
Yade T, Nakano T (2006) J Polym Sci A Polym Chem 44:561
Nakano T, Yade T (2008) Chem Lett 37:258–259
Nakano T, Tanikawa M, Nakagawa O, Yade T, Sakamoto T (2009) J Polym Sci A Polym Chem 47:239
García Martínez A, Osío Barcina J, de Fresno CA, Schlüter AD, Frahn J (1999) Adv Mater 11:27
Caraballo-Martínez N, Colorado Heras MR, Mba Blázquez M, Osío Barcina J, García Martínez A, Torres Salvador MR (2007) Org Lett 9:2943
Osío Barcina J, Colorado Heras MR, Mba M, Gómez Aspe R, Herrero-García N (2009) J Org Chem 74:7148
Bartholomew GP, Bazan GC (2001) Acc Chem Res 34:30
Oldham WJ Jr, Miao YJ, Lachicotte RJ, Bazan GC (1998) J Am Chem Soc 120:419
Bazan GC, Oldham WJ Jr, Lachicotte RJ, Tretiak S, Chernyak V, Mukamel S (1998) J Am Chem Soc 120:9188
Wang S, Bazan GC, Tretiak S, Mukamel S (2000) J Am Chem Soc 122:1289
Bartholomew GP, Bazan GC (2002) J Am Chem Soc 124:5183
Bartholomew GP, Bazan GC (2002) Synthesis 1245
Ruseckas A, Namdas EB, Lee JY, Mukamel S, Wang S, Bazan GC, Sundström V (2003) J Phys Chem A 107:8029–8034
Bazan GC (2007) J Org Chem 72:8645
Förster T (1946) Naturwissenschaften 33:166
van der Laan GP, de Haas MP, Hummel A, Frey H, Sheiko S, Möller M (1994) Macromolecules 27:1897
Hoofman RJOM, de Haas MP, Siebbeles LDA, Warman JM (1998) Nature 392:54
Warman JM, Gelinck GH, de Haas MP (2002) J Phys Condens Matter 14:9935
Grozema FC, Siebbeles LDA, Warman JM, Seki S, Tagawa S, Scherf U (2002) Adv Mater 14:228
Kocherzhenko AA, Patwardhan S, Grozema FC, Anderson HL, Siebbeles LDA (2009) J Am Chem Soc 131:5522
Pingel P, Zen A, Abellón RD, Grozema FC, Siebbeles LDA, Neher D (2010) Adv Funct Mater 20:2286
Saeki A, Tsuji M, Seki S (2011) Adv Energy Mater 1:661
Saeki A, Seki S, Shimizu Y, Yamao T, Hotta S (2010) J Chem Phys 132:134509–134511
Prasanthkumar S, Saeki A, Seki S, Ajayaghosh A (2010) J Am Chem Soc 132:8866
Yamamoto Y, Zhang G, Jin W, Fukushima T, Ishii N, Saeki A, Seki S, Tagawa S, Minari T, Tsukagoshi K, Aida T (2009) Proc Natl Acad Sci 106:21051
Saeki A, Seki S, Takenobu T, Iwasa Y, Tagawa S (2008) Adv Mater 20:920
Saeki A, Fukumatsu T, Seki S (2011) Macromolecules 44:3416
Fratiloiu S, Grozema FC, Koizumi Y, Seki S, Saeki A, Tagawa S, Dudek SP, Siebbeles LDA (2006) J Phys Chem B 110:5984
Feng X, Marcon V, Pisulal W, Hansen MR, Kirkpatrick J, Grozema F, Andrienko D, Kremer K, Müllen K (2009) Nat Mater 8:421
Morisaki Y, Lin L, Chujo Y (2009) Chem Lett 38:734
Morisaki Y, Lin L, Chujo Y (2009) J Polym Sci A Polym Chem 47:5979
Greenham NC, Moratti SC, Bradley DDC, Friend RH, Holmes AB (1993) Nature 365:628
Lin L, Morisaki Y, Chujo Y (2010) Int J Polym Sci 2010:908128
Walker SD, Barder TE, Martinelli JR, Buchwald SL (2004) Angew Chem Int Ed 43:1871
Reich HJ, Cram DJ (1969) J Am Chem Soc 91:3517
Bondarenko L, Dix I, Hinrichs H, Hopf H (2004) Synthesis 16:2751
Morisaki Y, Wada N, Arita M, Chujo Y (2009) Polym Bull 62:305
Cram DJ, Laainger NL (1955) J Am Chem Soc 77:6289
Rozenberg V, Sergeeva E, Hopf H (2004) In: Gleiter R, Hopf H (eds) Modern cyclophane chemistry. Wiley-VCH, Weinheim, pp 435–462
Rowlands GJ (2008) Org Biomol Chem 6:1527
Gibson SE, Knight JD (2003) Org Biomol Chem 1:1256
Aly AA, Brown AB (2009) Tetrahedron 65:8055
Paradies J (2011) Synthesis 3749
Pye PJ, Rossen K, Reamer RA, Tsou NN, Volante RP, Reider PJ (1997) J Am Chem Soc 119:6207
Rossen K, Pye PJ, Maliakal A, Volante RP (1997) J Org Chem 62:6462
Zhuravsky R, Starikova Z, Vorontsov E, Rozenberg V (2008) Tetrahedron Asym 19:216
Jiang B, Zhao XL (2004) Tetrahedron Asym 15:1141
Jones PG, Hillmer J, Hopf H (2003) Acta Crystallogr E59:o24
Pamperin D, Hopf H, Syldatk C, Pietzsch M (1997) Tetrahedron Asym 8:319
Pamperin D, Ohse B, Hopf H, Pietzsch M (1998) J Mol Cat B Enzym 5:317
Braddock DC, MacGilp ID, Perry BG (2002) J Org Chem 67:8679
Morisaki Y, Hifumi R, Lin L, Inoshita K, Chujo Y (2012) Chem Lett 41:990
Hitchcock PB, Rowlands GJ, Parmar R (2005) Chem Commun 4219
Parmar R, Coles MP, Hitchcock PB, Rowlands GJ (2010) Synthesis 4177
Lockard JP, Schroeck CW, Johnson CR (1973) Synthesis 485
Morisaki Y, Hifumi R, Lin L, Inoshita K, Chujo Y (2012) Polym Chem 3:2727
Satrijio A, Meskers SCJ, Swager TM (2006) J Am Chem Soc 128:9030
Wilson JN, Steffen W, McKenzie TG, Lieser G, Oda M, Neher D, Bunz UHF (2002) J Am Chem Soc 124:6830
Oda M, Nothofer HG, Lieser G, Scherf U, Meskers SCJ, Neher D (2000) Adv Mater 12:362
Oda M, Nothofer HG, Scherf U, Šunjic V, Richter D, Regenstein W, Meskers SCJ, Neher D (2002) Macromolecule 35:6792
Yu JM, Sakamoto T, Watanabe K, Furumi S, Tamaoki N, Chen Y, Nakano T (2011) Chem Commun 47:3799
Watanabe K, Sakamoto T, Taguchi M, Fujiki M, Nakano T (2011) Chem Commun 47:10996
Peeters E, Christiaans MPT, Janssen RAJ, Schoo HFM, Dekkers HPJM, Meijer EW (1997) J Am Chem Soc 119:9909
Langeveld-Voss BMW, Janssen RA, Christiaans MPT, Meskers SCJ, Dekkers HPJM, Meijer EW (1996) J Am Chem Soc 118:4908
Fukao S, Fujiki M (2009) Macromolecules 42:8062
Goto H, Akagi K (2005) Angew Chem Int Ed 44:4322
Hayasaka H, Miyashita T, Tamura K, Akagi K (2010) Adv Funct Mater 20:1243
Nakano Y, Liu Y, Fujiki M (2010) Polym Chem 1:460
Kawagoe Y, Fujiki M, Nakano Y (2010) New J Chem 34:637
Jagtap SP, Collard DM (2010) J Am Chem Soc 132:12208
Jagtap SP, Collard DM (2012) Polym Chem 3:463
Li H, Eddaoudi M, O'Keeffe M, Yaghi OM (1999) Nature 402:276
Cheetham AK, Férey G, Loiseau T (1999) Angew Chem Int Ed 38:3268
Eddaoudi M, Kim J, Rosi N, Vodak D, O'Keeffe M, Yaghi OM (2002) Science 295:469
Yaghi OM, O'Keeffe M, Ockwig NW, Chae HK, Eddaoudi M, Kim J (2003) Nature 423:705
Matzger A, O'Keeffe M, Yaghi OM (2004) Nature 427:523
Kitagawa S, Kitaura R, Noro S (2004) Angew Chem Int Ed 43:2334
Kitagawa S, Noro S, Nakamura T (2006) Chem Commun 701
Kitagawa S, Matsuda R (2007) Coord Chem Rev 251:2490
Maji TK, Kitagawa S (2007) Pure Appl Chem 79:2155
Férey G (2008) Chem Soc Rev 37:191
Uemura T, Yanai N, Kitagawa S (2009) Chem Soc Rev 38:1228
Jiang JX, Cooper AI (2010) Top Curr Chem 293:1
Thomas A (2010) Angew Chem Int Ed 49:8328
Thomas A, Kuhn P, Weber J, Titirici MM, Antonietti M (2009) Macromol Rapid Commun 30:221
McKeown NB, Budd PM (2006) Chem Soc Rev 35:675
Cooper AI (2009) Adv Mater 21:1291
Jiang JX, Su F, Trewin A, Wood CD, Campbell NL, Niu H, Dikckinson C, Ganin AY, Rosseinsky MJ, Khimyak YJ, Cooper AI (2007) Angew Chem Int Ed 46:8574
Jiang JX, Su F, Trewin A, Wood CD, Niu H, Jones TA, Khimyak YZ, Cooper AI (2008) J Am Chem Soc 130:7710
Jiang JX, Su F, Niu H, Wood CD, Campbell NL, Khimyak YZ, Cooper AI (2008) Chem Commun 486
Dawson R, Su F, Niu H, Wood CD, Jones JTA, Khimyak YZ, Cooper AI (2008) Macromolecules 41:1591
Palkovits R, Antonietti M, Kuhn P, Thomas A, Schüth F (2009) Angew Chem Int Ed 48:6909
Chen L, Honsho Y, Seki S, Jiang DL (2010) J Am Chem Soc 132:6742
Jiang JX, Laybourn A, Clowes R, Khimyak YZ, Bacsa J, Higgins SJ, Adams DJ, Cooper AI (2010) Macromolecules 43:7577
Dawson R, Laybourn A, Khimyak YZ, Adams DJ, Cooper AI (2010) Macromolecules 43:8524
Jiang JX, Wang C, Laybourn A, Hassell T, Clowes R, Khimyak YZ, Xiao J, Higgins SJ, Adams DJ, Cooper AI (2011) Angew Chem Int Ed 50:1072
Morisaki Y, Gon M, Tsuji Y, Kajiwara Y, Chujo Y (2011) Tetrahedron Lett 52:5504
Morisaki Y, Gon M, Tsuji Y, Kajiwara Y, Chujo Y (2012) Macromol Chem Phys 213:572
Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquérol J, Siemieniewska T (1985) Pure Appl Chem 57:603
Acknowledgments
Our works introduced herein are mainly supported by Grant-in-Aid for Young Scientists (B) (No. 16750096) and Young Scientists (A) (No. 21685012 and No. 24685018) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer
About this chapter
Cite this chapter
Morisaki, Y., Chujo, Y. (2014). Cyclophane-Based π-Stacked Polymers. In: Nakano, T. (eds) π-Stacked Polymers and Molecules. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54129-5_3
Download citation
DOI: https://doi.org/10.1007/978-4-431-54129-5_3
Published:
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-54128-8
Online ISBN: 978-4-431-54129-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)