Impact of Alkyl Spacer Length on Aggregation Pathways in Kinetically Controlled Supramolecular Polymerization

Journal of the American Chemical Society

Volumn 138, Issue 2, 2016, Pages 670-678

  Ogi, Soichiro ^a   Stepanenko, Vladimir ^a   Thein, Johannes ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; AGGREGATES; AMIDES; CHAINS; ETHYLENE; HYDROGEN BONDS; MONOMERS; POLYMERIZATION; SUPRAMOLECULAR CHEMISTRY;

INTRAMOLECULAR HYDROGEN BONDING; KINETICALLY CONTROLLED; PERYLENE BISIMIDES; PI-CONJUGATED SYSTEM; POLYMERIZATION PROCESS; SUPRAMOLECULAR POLYMERIZATION; SUPRAMOLECULAR POLYMERS; THERMODYNAMICALLY STABLE;

KINETICS;

ALKYL GROUP; AMIDE; ETHYLENE DERIVATIVE; HYDROGEN; IMIDE; MONOMER; NANOFIBER; NANOPARTICLE; PENTYLENE; PERYLENE BISIMIDE DERIVATIVE; POLYMER; PROPYLENE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL REACTION KINETICS; CHIRALITY; CONFORMATION; HYDROGEN BOND; MOLECULAR STABILITY; POLYMERIZATION; QUANTUM YIELD; SUPRAMOLECULAR CHEMISTRY; SUPRAMOLECULAR POLYMERIZATION; THERMODYNAMICS;

EID: 84955622355     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b11674     Document Type: Article

References (51)

1. Yang, L.; Tan, X.; Wang, Z.; Zhang, X. Chem. Rev. 2015, 115, 7196-7239 10.1021/cr500633b
2. Rest, C.; Kandanelli, R.; Fernández, G. Chem. Soc. Rev. 2015, 44, 2543-2572 10.1039/C4CS00497C
3. Würthner, F. Nat. Chem. 2014, 6, 171-173 10.1038/nchem.1863
4. Van der Zwaag, D.; De Greef, T. F. A.; Meijer, E. W. Angew. Chem., Int. Ed. 2015, 54, 8334-8336 10.1002/anie.201503104
5. Mukhopadhyay, R. D.; Ajayaghosh, A. Science 2015, 349, 241-242 10.1126/science.aac7422
6. Tidhar, Y.; Weissman, H.; Wolf, S. G.; Gulino, A.; Rybtchinski, B. Chem.-Eur. J. 2011, 17, 6068-6075 10.1002/chem.201003419
7. Rybtchinski, B. ACS Nano 2011, 5, 6791-6818 10.1021/nn2025397
8. Rosen, B. M.; Peterca, M.; Morimitsu, K.; Dulcey, A. E.; Leowanawat, P.; Resmerita, A.-M.; Imam, M. R.; Percec, V. J. Am. Chem. Soc. 2011, 133, 5135-5151 10.1021/ja200280h
9. Roche, C.; Sun, H.-J.; Prendergast, M. E.; Leowanawat, P.; Partridge, B. E.; Heiney, P. A.; Araoka, F.; Graf, R.; Spiess, H. W.; Zeng, X.; Ungar, G.; Percec, V. J. Am. Chem. Soc. 2014, 136, 7169-7185 10.1021/ja5035107
10. Korevaar, P. A.; Newcomb, C. J.; Meijer, E. W.; Stupp, S. I. J. Am. Chem. Soc. 2014, 136, 8540-8543 10.1021/ja503882s
11. De Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A. P. H. J.; Sijbesma, R. P.; Meijer, E. W. Chem. Rev. 2009, 109, 5687-5754 10.1021/cr900181u
12. Ogi, S.; Sugiyasu, K.; Manna, S.; Samitsu, S.; Takeuchi, M. Nat. Chem. 2014, 6, 188-195 10.1038/nchem.1849
13. Wang, X.; Guerin, G.; Wang, H.; Wang, Y.; Manners, I.; Winnik, M. A. Science 2007, 317, 644-647 10.1126/science.1141382
14. Gilroy, J. B.; Gädt, T.; Whittell, G. R.; Chabanne, L.; Mitchels, J. M.; Richardson, R. M.; Winnik, M. A.; Manners, I. Nat. Chem. 2010, 2, 566-570 10.1038/nchem.664
15. Patra, S. K.; Ahmed, R.; Whittell, G. R.; Lunn, D. J.; Dunphy, E. L.; Winnik, M. A.; Manners, I. J. Am. Chem. Soc. 2011, 133, 8842-8845 10.1021/ja202408w
16. Robinson, M. E.; Lunn, D. J.; Nazemi, A.; Whittell, G. R.; De Cola, L.; Manners, I. Chem. Commun. 2015, 51, 15921-15924 10.1039/C5CC06606A
17. Pal, A.; Malakoutikhah, M.; Leonetti, G.; Tezcan, M.; Colomb-Delsuc, M.; Nguyen, V. D.; van der Gucht, J.; Otto, S. Angew. Chem., Int. Ed. 2015, 54, 7852-7856 10.1002/anie.201501965
18. Kasai, M.; Asakura, S.; Oosawa, F. Biochim. Biophys. Acta 1962, 57, 22-31 10.1016/0006-3002(62)91073-9
19. Asakura, S.; Eguchi, G.; Iino, T. J. Mol. Biol. 1964, 10, 42-56 10.1016/S0022-2836(64)80026-7
20. Zhao, D.; Moore, J. S. Org. Biomol. Chem. 2003, 1, 3471-3491 10.1039/b308788c
21. Zhang, W.; Jin, W.; Fukushima, T.; Saeki, A.; Seki, S.; Aida, T. Science 2011, 334, 340-343 10.1126/science.1210369
22. Zhang, W.; Jin, W.; Fukushima, T.; Mori, T.; Aida, T. J. Am. Chem. Soc. 2015, 137, 13792-13795 10.1021/jacs.5b09878
23. Mattia, E.; Otto, S. Nat. Nanotechnol. 2015, 10, 111-119 10.1038/nnano.2014.337
24. Kang, J.; Miyajima, D.; Itoh, Y.; Mori, T.; Tanaka, H.; Yamauchi, M.; Inoue, Y.; Harada, S.; Aida, T. J. Am. Chem. Soc. 2014, 136, 10640-10644 10.1021/ja505941b
25. Kang, J.; Miyajima, D.; Mori, T.; Inoue, Y.; Itoh, Y.; Aida, T. Science 2015, 347, 646-651 10.1126/science.aaa4249
26. Ogi, S.; Stepanenko, V.; Sugiyasu, K.; Takeuchi, M.; Würthner, F. J. Am. Chem. Soc. 2015, 137, 3300-3307 10.1021/ja511952c
27. Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173 10.1021/ja00004a016
28. Nowick, J. S.; Abdi, M.; Bellamo, A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89-99 10.1021/ja00106a011
29. Baldwin, R. L. Folding Des. 1996, 1, R1-R8 10.1016/S1359-0278(96)00003-X
30. van der Zwaag, D.; Pieters, P. A.; Korevaar, P. A.; Markvoort, A. J.; Spiering, A. J. H.; de Greef, T. F. A.; Meijer, E. W. J. Am. Chem. Soc. 2015, 137, 12677-12688 10.1021/jacs.5b08138
31. Li, X.-Q.; Stepanenko, V.; Chen, Z.; Prins, P.; Siebbeles, L. D. A.; Würthner, F. Chem. Commun. 2006, 3871-3873 10.1039/b611422a
32. Ghosh, S.; Li, X.-Q.; Stepanenko, V.; Würthner, F. Chem.-Eur. J. 2008, 14, 11343-11357 10.1002/chem.200801454
33. Stepanenko, V.; Li, X.-Q.; Gershberg, J.; Würthner, F. Chem.-Eur. J. 2013, 19, 4176-4183 10.1002/chem.201204146
34. Würthner, F.; Thalacker, C.; Sautter, A.; Schärtl, W.; Ibach, W.; Hollricher, O. Chem.-Eur. J. 2000, 6, 3871-3886 10.1002/1521-3765(20001103)6:21<3871::AID-CHEM3871>3.3.CO;2-W
35. Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem.-Eur. J. 2001, 7, 2245-2253 10.1002/1521-3765(20010518)7:10<2245::AID-CHEM2245>3.0.CO;2-W
36. Würthner, F.; Chen, Z.; Dehm, V.; Stepanenko, V. Chem. Commun. 2006, 1188-1190 10.1039/b517020f
37. Marcus, R. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1111-1222 10.1002/anie.199311113
38. Polese, A.; Mondini, S.; Bianco, A.; Toniolo, C.; Scorrano, G.; Guldi, D. M.; Maggini, M. J. Am. Chem. Soc. 1999, 121, 3446-3452 10.1021/ja983421d
39. Sisido, M.; Hoshino, S.; Kusano, H.; Kuragaki, M.; Makino, M.; Sasaki, H.; Smith, T. A.; Ghiggino, K. P. J. Phys. Chem. B 2001, 105, 10407-10415 10.1021/jp011180h
40. Jonkheijm, P.; van der Schoot, P.; Schenning, A. P. H. J.; Meijer, E. W. Science 2006, 313, 80-83 10.1126/science.1127884
41. Smulders, M. M. J.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2008, 130, 606-611 10.1021/ja075987k
42. Smulders, M. M. J.; Nieuwenhuizen, M. M. L.; de Greef, T. F. A.; van der Schoot, P.; Schenning, A. P. H. J.; Meijer, E. W. Chem.-Eur. J. 2010, 16, 362-367 10.1002/chem.200902415
43. Bachmann, P. A.; Luisi, P. L.; Lang, J. Nature 1992, 357, 57-59 10.1038/357057a0
44. Lohr, A.; Würthner, F. Angew. Chem., Int. Ed. 2008, 47, 1232-1236 10.1002/anie.200704550
45. Carnall, J. M. A.; Waudby, C. A.; Belenguer, A. M.; Stuart, M. C. A.; Peyralans, J. J.-P.; Otto, S. Science 2010, 327, 1502-1506 10.1126/science.1182767
46. Baram, J.; Weissman, H.; Rybtchinski J. Phys. Chem. B 2014, 118, 12068-12073 10.1021/jp507945t
47. Cui, H. G.; Chen, Z. Y.; Zhong, S.; Wooley, K. L.; Pochan, D. J. Science 2007, 317, 647-650 10.1126/science.1141768
48. Korevaar, P. A.; George, S. J.; Markvoort, A. J.; Smulders, M. M. J.; Hilbers, P. A. J.; Schenning, A. P. H. J.; De Greef, T. F. A.; Meijer, E. W. Nature 2012, 481, 492-496 10.1038/nature10720
49. Babu, S. S.; Praveen, V. K.; Ajayaghosh, A. Chem. Rev. 2014, 114, 1973-2129 10.1021/cr400195e
50. Molla, M. R.; Ghosh, S. Chem. Mater. 2011, 23, 95-105 10.1021/cm102343r
51. Li, J.-L.; Liu, X.-Y. Adv. Funct. Mater. 2010, 20, 3196-3216 10.1002/adfm.201000744