Water-soluble cruciforms and distyrylbenzenes: Synthesis, characterization, and pH-dependent amine-sensing properties

Journal of Organic Chemistry

Volumn 78, Issue 10, 2013, Pages 4949-4959

  Freudenberg, Jan ^a   Kumpf, Jan ^a   Schäfer, Vera ^a   Sauter, Eric ^a   Wörner, Svenja J ^a   Brödner, Kerstin ^a   Dreuw, Andreas ^a   Bunz, Uwe H F ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIAMINOPROPANE; DETECTION LIMITS; DISTYRYLBENZENE DERIVATIVES; ETHER BRIDGES; OLIGOETHYLENE GLYCOLS; PH-DEPENDENT; PRIMARY AMINES; WATER SOLUBILITIES;

ALKALINITY; AMINO ACIDS; FLUORESCENCE; NITROGEN COMPOUNDS;

ALDEHYDES;

1,3 PROPANEDIAMINE; ALDEHYDE; AMINE; BENZENE DERIVATIVE; CYSTEINE; DISTYRYLBENZENE DERIVATIVE; IMINE; LYSINE; MACROGOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE; LIMIT OF DETECTION; PH; SOLUBILITY; SYNTHESIS;

ALDEHYDES; AMINES; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; SOLUBILITY; STYRENES; WATER;

EID: 84878080225     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400576y     Document Type: Article

References (52)

1. Phillips, R. L.; Kim, I. B.; Tolbert, L. M.; Bunz, U. H. F. J. Am. Chem. Soc. 2008, 130, 6952-6955
2. Merchant, Z. M.; Cheng, S. G. G. In Characterization of Foods, Emerging Methods; Gaonkar, A. G., Ed.; Elsevier Science: New York, 1995; Chapter 15.
3. Bao, B.; Yuwen, L.; Zheng, X.; Weng, L.; Zhu, X.; Zhan, X.; Wang, L. J. Mater. Chem. 2010, 20, 9628-9634
4. Ajayakumar, M. R.; Mukhopadhyay, P. Chem. Commun. 2009, 3702-3704
5. Kçrsten, S.; Mohr, G. J. Chem. Eur. J. 2011, 17, 969-975
6. Mohr, G. J. Chem. Eur. J. 2004, 10, 1082-1090
7. Mohr, G. J.; Demuth, C.; Spichinger-Keller, U. E. Anal. Chem. 1998, 70, 3868-3873
8. Rakow, N. A.; Sen, A.; Janzen, M. C.; Ponder, J. B.; Suslick, K. S. Angew. Chem. 2005, 117, 4604-4608
9. Angew. Chem., Int. Ed. 2005, 44, 4528-4532.
10. Greene, N. T.; Shimizu, K. D. J. Am. Chem. Soc. 2005, 127, 5695-5700
11. Merchant, Z. M.; Cheng, S. G. G. In Characterization of Foods, Emerging Methods; Gaonkar, A. G., Ed.; Elsevier Science: New York, 1995; Chapter 15.
12. Zhou, H. C.; Baldini, L.; Hong, J.; Wilson, A. J.; Hamilton, A. D. J. Am. Chem. Soc. 2006, 128, 2421-2425
13. Yeh, C. Y.; Lin, S. J.; Hwang, D. F. J. Food Drug Anal. 2004, 12, 128-132
14. Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972
15. Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666-3669
16. Bao, B.; Yuwen, L.; Zheng, X.; Weng, L.; Zhu, X.; Zhan, X.; Wang, L. J. Mater. Chem. 2010, 20, 9628-9634
17. Ajayakumar, M. R.; Mukhopadhyay, P. Chem. Commun. 2009, 3702-3704
18. Kçrsten, S.; Mohr, G. J. Chem. Eur. J. 2011, 17, 969-975
19. Mohr, G. J. Chem. Eur. J. 2004, 10, 1082-1090
20. Mohr, G. J.; Demuth, C.; Spichinger-Keller, U. E. Anal. Chem. 1998, 70, 3868-3873
21. Nelson, T. L.; Osullivan, C.; Greene, N. T.; Maynor, M. S.; Lavigne, J. J. J. Am. Chem. Soc. 2006, 128, 5640-5641
22. Maynor, M. S.; Nelson, T. L.; Osullivan, C.; Lavigne, J. J. Org. Lett. 2007, 9, 3217-3220
23. Nelson, T. L.; Tran, I.; Ingallinera, T. G.; Maynor, M. S.; Lavigne, J. J. Analyst 2007, 132, 1024-1030
24. Mertz, E.; Zimmerman, S. C. J. Am. Chem. Soc. 2003, 125, 3424-3425
25. Mertz, E.; Beil, J. B.; Zimmerman, S. C. Org. Lett. 2003, 5, 3127-3130
26. Feustler, E. K.; Glass, T. E. J. Am. Chem. Soc. 2003, 125, 16174-16175
27. Secor, K.; Plante, J.; Avetta, C.; Glass, T. E. J. Mater. Chem. 2005, 15, 4073-4077
28. Kumpf, J.; Bunz, U. H. F. Chem. Eur. J. 2012, 18, 8921-8924
29. Zucchero, A. J.; McGrier, P. L.; Bunz, U. H. F. Acc. Chem. Res. 2010, 43, 397-408
30. Hauck, M.; Schönhaber, J.; Zucchero, A. J.; Hardcastle, K. I.; Müller, T. J. J.; Bunz, U. H. F. J. Org. Chem. 2007, 72, 6714-6725
31. Zucchero, A. J.; Wilson, J. N.; Bunz, U. H. F. J. Am. Chem. Soc. 2006, 128, 11872-11881
32. Davey, E. A.; Zucchero, A.; Trapp, O.; Bunz, U. H. F. J. Am. Chem. Soc. 2011, 133, 7716-7718
33. Schwaebel, T.; Trapp, O.; Bunz, U. H. F. Chem. Sci. 2013, 4, 273-281
34. Gerhardt, W. W.; Zucchero, A. J.; Wilson, J. N.; South, C. R.; Bunz, U. H. F.; Weck, M. Chem. Commun. 2006, 2141-2143
35. Tolosa, J.; Solntsev, K. M.; Tolbert, L. M.; Bunz, U. H. F. J. Org. Chem. 2010, 75, 523-534
36. Tolosa, J.; Zucchero, A. J.; Bunz, U. H. F. J. Am. Chem. Soc. 2008, 130, 6498-6506
37. McGrier, P. L.; Solntsev, K. M.; Miao, S.; Tolbert, L. M.; Miranda, O. R.; Rotello, V. M.; Bunz, U. H. F. Chem. Eur. J. 2008, 14, 4503-4510
38. Patze, C.; Broedner, K.; Rominger, F.; Trapp, O.; Bunz, U. H. F. Chem. Eur. J. 2011, 17, 13720-13725
39. Schwaebel, T.; Schäfer, V.; Wenz, J.; Coombs, B. A.; Tolosa, J.; Bunz, U. H. F. J. Org. Chem. 2013, 78, 960-965
40. Wilson, J. N.; Windscheif, P. M.; Evans, U.; Myrick, M. L.; Bunz, U. H. F. Macromolecules 2002, 35, 8681-8683
41. Casida, M. E. In Recent Advances in Density Functional Theory; Chong, D. P., Ed.; World Scientific: Singapore, 1995; Part I, pp 145-192.
42. Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009-4037
43. Neese, F. WIREs Comput. Mol. Sci. 2012, 2, 73-78
44. Schäfer, A.; Klamt, A.; Sattel, D.; Lohrenz, J. C. W.; Eckert, F. Phys. Chem. Chem. Phys. 2000, 2, 2187-2192
45. Plötner, J.; Tozer, D. J.; Dreuw, A. J. Chem. Theo. Comp. 2010, 6, 2315-2324
46. Head-Gordon, M.; Grana, A. M.; Maurice, D.; White, C. A. J. Phys. Chem. 1995, 99, 14261-14268
47. Sprung, M. M. Chem. Rev. 1940, 26, 297-336
48. Layer, R. W. Chem. Rev. 1963, 63, 489-510
49. Dayagi, S. In The chemistry of the carbon-nitrogen double bond; Patai, S., Ed.; Wiley: New York, 1970; pp 61-147.
50. Yasuda, T.; Shimizu, T.; Liu, F.; Ungar, G.; Kato, T. J. Am. Chem. Soc. 2011, 133, 13437-13444
51. Winter, A.; Friebe, C.; Hager, M. D.; Schubert, U. S. Eur. J. Org. Chem. 2009, 801-809
52. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176-2179