Correction to "chiral Conjugated Corrals" (J. Am. Chem. Soc. (2015) 137 (9982-9987) DOI: 10.1021/jacs.5b05698);Chiral Conjugated Corrals

Journal of the American Chemical Society

Volumn 137, Issue 31, 2015, Pages 9982-9987

  Ball, Melissa ^b   Fowler, Brandon ^b   Li, Panpan ^a,b   Joyce, Leo A ^c   Li, Fang ^a   Liu, Taifeng ^a   Paley, Daniel ^b   Zhong, Yu ^b   Li, Hexing ^a   Xiao, Shengxiong ^a   Ng, Fay ^b   Steigerwald, Michael L ^b   Nuckolls, Colin ^a,b  

^a SHANGHAI NORMAL UNIVERSITY   (China)

^b Columbia University ^*  (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSITIONS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLYCYCLIC AROMATIC HYDROCARBONS;

CHEMICAL EQUATIONS; CHIRAL HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIES; DESIGN MOTIFS; ELECTRON DONORS; INTERCONVERSIONS; PERYLENEDIIMIDES; PHOTO-INDUCED ELECTRON TRANSFER; TRANSVERSE AXIS;

STEREOCHEMISTRY;

MACROCYCLIC COMPOUND; PERYLENE; THIOPHENE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHIRALITY; CONJUGATION; DENSITY FUNCTIONAL THEORY; ELECTRON; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR DYNAMICS; STEREOISOMERISM; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG DESIGN; MECHANICAL STRESS;

DRUG DESIGN; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; STRESS, MECHANICAL;

EID: 84939222042     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b00013     Document Type: Erratum

References (56)

1. Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 17646 10.1021/ja807126u
2. Evans, P. J.; Darzi, E. R.; Jasti, R. Nat. Chem. 2014, 6, 404 10.1038/nchem.1888
3. Omachi, H.; Matsuura, S.; Segawa, Y.; Itami, K. Angew. Chem., Int. Ed. 2010, 49, 10202 10.1002/anie.201005734
4. Segawa, Y.; Miyamoto, S.; Omachi, H.; Matsuura, S.; Šenel, P.; Sasamori, T.; Tokitoh, N.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 3244 10.1002/anie.201007232
5. Segawa, Y.; Šenel, P.; Matsuura, S.; Omachi, H.; Itami, K. Chem. Lett. 2011, 40, 423 10.1246/cl.2011.423
6. Omachi, H.; Segawa, Y.; Itami, K. Org. Lett. 2011, 13, 2480 10.1021/ol200730m
7. Omachi, H.; Segawa, Y.; Itami, K. Acc. Chem. Res. 2012, 45, 1378 10.1021/ar300055x
8. Ishii, Y.; Nakanishi, Y.; Omachi, H.; Matsuura, S.; Matsui, K.; Shinohara, H.; Segawa, Y.; Itami, K. Chem. Sci. 2012, 3, 2340 10.1039/c2sc20343j
9. Yamago, S.; Watanabe, Y.; Iwamoto, T. Angew. Chem., Int. Ed. 2010, 49, 757 10.1002/anie.200905659
10. Iwamoto, T.; Watanabe, Y.; Sadahiro, T.; Haino, T.; Yamago, S. Angew. Chem., Int. Ed. 2011, 50, 8342 10.1002/anie.201102302
11. Iwamoto, T.; Watanabe, Y.; Sakamoto, Y.; Suzuki, T.; Yamago, S. J. Am. Chem. Soc. 2011, 133, 8354 10.1021/ja2020668
12. Kayahara, E.; Sakamoto, Y.; Suzuki, T.; Yamago, S. Org. Lett. 2012, 14, 3284 10.1021/ol301242t
13. Iwamoto, T.; Kayahara, E.; Yasuda, N.; Suzuki, T.; Yamago, S. Angew. Chem., Int. Ed. 2014, 53, 6430 10.1002/anie.201403624
14. Kayahara, E.; Patel, V. K.; Yamago, S. J. Am. Chem. Soc. 2014, 136, 2284 10.1021/ja413214q
15. Yamago, S.; Kayahara, E.; Iwamoto, T. Chem. Rec. 2014, 14, 84 10.1002/tcr.201300035
16. Hitosugi, S.; Nakanishi, W.; Isobe, H. Chem.-Asian J. 2012, 7, 1550 10.1002/asia.201200187
17. Hitosugi, S.; Yamasaki, T.; Isobe, H. J. Am. Chem. Soc. 2012, 134, 12442 10.1021/ja305723j
18. O'Sullivan, M. C.; Sprafke, J. K.; Kondratuk, D. V.; Rinfray, C.; Claridge, T. D. W.; Saywell, A.; Blunt, M. O.; O'Shea, J. N.; Beton, P. H.; Malfois, M.; Anderson, H. L. Nature 2011, 469, 72 10.1038/nature09683
19. Neuhaus, P.; Cnossen, A.; Gong, J. Q.; Herz, L. M.; Anderson, H. L. Angew. Chem., Int. Ed. 2015, 54, 7344 10.1002/anie.201502735
20. Jiang, H. W.; Tanaka, T.; Mori, H.; Park, K. H.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2015, 137, 2219 10.1021/ja513102m
21. Nishihara, T.; Segawa, Y.; Itami, K.; Kanemitsu, Y. J. Phys. Chem. Lett. 2012, 3, 3125 10.1021/jz3014826
22. Camacho, C.; Niehaus, T. A.; Itami, K.; Irle, S. Chem. Sci. 2013, 4, 187 10.1039/C2SC20878D
23. Alvarez, M. P.; Burrezo, P. M.; Kertesz, M.; Iwamoto, T.; Yamago, S.; Xia, J. L.; Jasti, R.; Navarrete, J. T. L.; Taravillo, M.; Baonza, V. G.; Casado, J. Angew. Chem., Int. Ed. 2014, 53, 7033 10.1002/anie.201400719
24. The smallest HOMO/LUMO gap in a CPP is seen in [5]-CPP, the smallest CPP synthesized to date. The HOMO/LUMO gap from calculations is 2.34 eV. See refs 2 and 12.
25. Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Polym. Bull. 1992, 29, 119 10.1007/BF00558045
26. Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Synth. Met. 1993, 55, 299 10.1016/0379-6779(93)90949-W
27. Leriche, P.; Frère, P.; Cravino, A.; Alévêque, O.; Roncali, J. J. Org. Chem. 2007, 72, 8332 10.1021/jo701390y
28. Anthony, J. E.; Facchetti, A.; Heeney, M.; Marder, S. R.; Zhan, X. W. Adv. Mater. 2010, 22, 3876 10.1002/adma.200903628
29. Nolde, F.; Pisula, W.; Müller, S.; Kohl, C.; Müllen, K. Chem. Mater. 2006, 18, 3715 10.1021/cm060742c
30. Zhong, Y.; Kumar, B.; Oh, S.; Trinh, M. T.; Wu, Y.; Elbert, K.; Li, P. P.; Zhu, X. Y.; Xiao, S. X.; Ng, F.; Steigerwald, M. L.; Nuckolls, C. J. Am. Chem. Soc. 2014, 136, 8122 10.1021/ja503533y
31. Ball, M.; Zhong, Y.; Wu, Y.; Schenck, C.; Ng, F.; Steigerwald, M.; Xiao, S. X.; Nuckolls, C. Acc. Chem. Res. 2015, 48, 267 10.1021/ar500355d
32. Zhou, E. J.; Cong, J. Z.; Wei, Q. S.; Tajima, K.; Yang, C. H.; Hashimoto, K. Angew. Chem., Int. Ed. 2011, 50, 2799 10.1002/anie.201005408
33. Li, C.; Wonneberger, H. Adv. Mater. 2012, 24, 613 10.1002/adma.201104447
34. Sharenko, A.; Proctor, C. M.; van der Poll, T. S.; Henson, Z. B.; Nguyen, T.-Q.; Bazan, G. C. Adv. Mater. 2013, 25, 4403 10.1002/adma.201301167
35. Cai, Y.; Huo, L.; Sun, X.; Wei, D.; Tang, M.; Sun, Y. Adv. Energy Mater. 2015, 5, 1500032
36. Huo, L. J.; Zhou, Y.; Li, Y. F. Macromol. Rapid Commun. 2008, 29, 1444 10.1002/marc.200800268
37. Yan, Q. F.; Zhao, D. H. Org. Lett. 2009, 11, 3426 10.1021/ol9012734
38. Roncali, J. Chem. Rev. 1992, 92, 711 10.1021/cr00012a009
39. Roncali, J. Macromol. Rapid Commun. 2007, 28, 1761 10.1002/marc.200700345
40. Zhang, F.; Götz, G.; Winkler, H. D. F.; Schalley, C. A.; Bäuerle, P. Angew. Chem., Int. Ed. 2009, 48, 6632 10.1002/anie.200900101
41. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508 10.1002/anie.198605081
42. Zhang, J. X.; Singh, S.; Hwang, D. K.; Barlow, S.; Kippelen, B.; Marder, S. R. J. Mater. Chem. C 2013, 1, 5093 10.1039/c3tc30918e
43. Rohr, U.; Kohl, C.; Müllen, K.; van de Craats, A.; Warman, J. J. Mater. Chem. 2001, 11, 1789 10.1039/b009708j
44. Chao, C.-C.; Leung, M.-K.; Su, Y. O.; Chiu, K.-Y.; Lin, T.-H.; Shieh, S.-J.; Lin, S.-C. J. Org. Chem. 2005, 70, 4323 10.1021/jo050001f
45. The 1,7-dibromo-PDI is synthesized from the parent anhydride according to known procedures. See ref 30.
46. The 1,6- and 1,7-regioisomers are present in the parent dibromo-PDI in a 1:5 ratio and, as a result, are present after the Stille coupling reaction to form 2. However, we are able to separate the regioisomers with chromatography and proceed with solely the 1,7-isomer to form 3. Details are contained the Supporing Information.
47. Eaborn, C.; Odell, K. J.; Pidcock, A. J. Chem. Soc., Dalton Trans. 1978, 357 10.1039/dt9780000357
48. We use branched undecyl side chains in order to enhance the solubility of the macrocycle. See refs 29 and 30.
49. Zhong, Y.; Trinh, M. T.; Chen, R. S.; Wang, W.; Khlyabich, P. P.; Kumar, B.; Xu, Q. Z.; Nam, C.-Y.; Sfeir, M. Y.; Black, C.; Steigerwald, M. L.; Loo, Y.-L.; Xiao, S. X.; Ng, F.; Zhu, X.-Y.; Nuckolls, C. J. Am. Chem. Soc. 2014, 136, 15215 10.1021/ja5092613
50. Rajasingh, P.; Cohen, R.; Shirman, E.; Shimon, L. J. W.; Rybtchinski, B. J. Org. Chem. 2007, 72, 5973 10.1021/jo070367n
51. See Supporting Information for the X-ray crystal structure of N,N'-di-(6-undecyl)-1,7-di(4-bromophenyl)perylene-3,4:9,10-tetracarboxylic diimide (Figure S2) and the.cif file.
52. Goretzki, G.; Davies, E. S.; Argent, S. P.; Warren, J. E.; Blake, A. J.; Champness, N. R. Inorg. Chem. 2009, 48, 10264 10.1021/ic901379d
53. Samdal, S.; Samuelsen, E. J.; Volden, H. V. Synth. Met. 1993, 59, 259 10.1016/0379-6779(93)91035-Z
54. Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L. Chem. Phys. Lett. 1993, 208, 120 10.1016/0009-2614(93)80088-7
55. Capozzi, B.; Dell, E. J.; Berkelbach, T. C.; Reichman, D. R.; Venkataraman, L.; Campos, L. M. J. Am. Chem. Soc. 2014, 136, 10486 10.1021/ja505277z
56. Ito, H.; Mitamura, Y.; Segawa, Y.; Itami, K. Angew. Chem., Int. Ed. 2015, 54, 159 10.1002/anie.201409389