Computational design, synthesis, and mechanochromic properties of new thiophene-based π-conjugated chromophores

Chemistry - A European Journal

Volumn 19, Issue 6, 2013, Pages 1996-2004

  Prampolini, Giacomo ^a   Bellina, Fabio ^b   Biczysko, Malgorzata ^c,d   Cappelli, Chiara ^b   Carta, Luciano ^d   Lessi, Marco ^b   Pucci, Andrea ^a,b   Ruggeri, Giacomo ^a,b   Barone, Vincenzo ^d  

^a AREA DELLA RICERCA   (Italy)

^b UNIVERSITY OF PISA   (Italy)

^c CENTER FOR NANOTECHNOLOGY INNOVATION NEST   (Italy)

^d SCUOLA NORMALE SUPERIORE   (Italy)

Author keywords

chromophores; computational design; dyes pigments; luminescence; mechanochromic materials

Indexed keywords

BENZENE; LUMINESCENCE; OPTICAL PROPERTIES; ORGANIC POLYMERS; SUPRAMOLECULAR CHEMISTRY; THIOPHENE;

COMPUTATIONAL DESIGN; COMPUTATIONAL INVESTIGATION; CORE STRUCTURE; DYES/PIGMENTS; ETHYNYL; EXPERIMENTAL TECHNIQUES; IN-SILICO; MECHANOCHROMIC PROPERTIES; NOVEL MATERIALS; POLYETHYLENE MATRIX; POLYMERIC MATRICES; SEQUENTIAL CROSS-COUPLING REACTIONS; SMART POLYMERS; SPECTRAL FEATURE; SPECTRAL PROPERTIES; SUPRAMOLECULAR ARCHITECTURES; VIRTUAL SCREENING;

CHROMOPHORES;

EID: 84962376420     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203672     Document Type: Article

References (54)

1. X. Zhang, S. Rehm, M. M. Safont-Sempere, F. Würthner, Nat. Chem. 2009, 1, 623-629
2. Y. Sagara, T. Kato, Nat. Chem. 2009, 1, 605-610
3. Y. Sagara, T. Kato, Angew. Chem. 2011, 123, 9294-9298
4. Angew. Chem. Int. Ed. 2011, 50, 9128-9132
5. P. Anzenbacher, F. Li, M. A. Palacios, Angew. Chem. 2012, 124, 2395
6. Angew. Chem. Int. Ed. 2012, 51, 2345.
7. J.-L. Bredas, S. R. Marder, E. Reichmanis, Chem. Mater. 2011, 23, 309-309.
8. A. Pucci, R. Bizzarri, G. Ruggeri, Soft Matter 2011, 7, 3689-3700
9. A. Pucci, G. Ruggeri, J. Mater. Chem. 2011, 21, 8282-8291.
10. D. A. Davis, A. Hamilton, J. L. Yang, L. D. Cremar, D. Van Gough, S. L. Potisek, M. T. Ong, P. V. Braun, T. J. Martinez, S. R. White, J. S. Moore, N. R. Sottos, Nature 2009, 459, 68-72
11. Y. Chen, A. J. H. Spiering, S. Karthikeyan, G. W. M. Peters, E. W. Meijer, R. P. Sijbesma, Nat. Chem. 2012, 4, 559-562.
12. C. Weder, J. Mater. Chem. 2011, 21, 8235-8236.
13. C. J. Cramer, Essentials of Computational Chemistry, 2 nd ed., Wiley, Chichester, 2004
14. P. Kirkpatrick, Nat. Rev. Drug Discovery 2005, 4, 959
15. M. Cifelli, L. De Gaetani, G. Prampolini, A. Tani, J. Phys. Chem. B 2008, 112, 9777-9786
16. M. McCullagh, T. Prytkova, S. Tonzani, N. D. Winter, G. C. Schatz, J. Phys. Chem. B 2008, 112, 10388-10398
17. L. R. Dalton, S. J. Benight, L. E. Johnson, D. B. Knorr, I. Kosilkin, B. E. Eichinger, B. H. Robinson, A. K. Y. Jen, R. M. Overney, Chem. Mater. 2011, 23, 430-445
18. S. Difley, L.-P. Wang, S. Yeganeh, S. R. Yost, T. V. Voorhis, Acc. Chem. Res. 2010, 43, 995-1004
19. D. Beljonne, J. Cornil, L. Muccioli, C. Zannoni, J.-L. Brèdas, F. Castet, Chem. Mater. 2011, 23, 591-609
20. A. Pedone, G. Prampolini, S. Monti, V. Barone, Phys. Chem. Chem. Phys. 2011, 13, 16689-16697
21. R. J. Macfarlane, B. Lee, M. R. Jones, N. Harris, G. C. Schatz, C. A. Mirkin, Science 2011, 334, 204-208
22. S. Fantacci, F. De Angelis, Coord. Chem. Rev. 2011, 255, 2704-2726
23. G. C. Schatz, J. Phys. Chem. Lett. 2011, 2, 125-126
24. L. Zhu, Y. Yi, Y. Li, E.-G. Kim, V. Coropceanu, J.-L. Brèdas, J. Am. Chem. Soc. 2012, 134, 2340-2347.
25. V. Barone, Computational Strategies for Spectroscopy: From Small Molecules to Nano Systems, Wiley, Hoboken, 2011.
26. V. Barone, J. Bloino, M. Biczysko, F. Santoro, J. Chem. Theory Comput. 2009, 5, 540-554
27. J. Bloino, M. Biczysko, F. Santoro, V. Barone, J. Chem. Theory Comput. 2010, 6, 1256-1274.
28. M. Usui, H. Fukumoto, T. Yamamoto, Bull. Chem. Soc. Jpn. 2010, 83, 1397.
29. J. Fortage, J. Boixel, E. Blart, L. Hammarström, H. C. Becker, F. Odobel, Chem. Eur. J. 2008, 14, 3467-3480.
30. A. Soheili, J. Albaneze-Walker, J. A. Murry, P. G. Dormer, D. L. Hughes, Org. Lett. 2003, 5, 4191-4194.
31. F. Bellina, M. Lessi, Synlett 2012, 23, 773-777.
32. N. Tirelli, S. Amabile, C. Cellai, A. Pucci, L. Regoli, G. Ruggeri, F. Ciardelli, Macromolecules 2001, 34, 2129-2137
33. A. Pucci, N. Tirelli, G. Ruggeri, F. Ciardelli, Macromol. Chem. Phys. 2005, 206, 102.
34. F. Santoro, R. Improta, A. Lami, J. Bloino, V. Barone, J. Chem. Phys. 2007, 126, 084509-084513.
35. G. Pietraperzia, M. Pasquini, F. Mazzoni, G. Piani, M. Becucci, M. Biczysko, D. Michalski, J. Bloino, V. Barone, J. Phys. Chem. A 2011, 115, 9603-9611
36. D. Jacquemin, E. Bremond, I. Ciofini, C. Adamo, J. Phys. Chem. Lett. 2012, 3, 468-471.
37. S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. Lett. 1981, 55, 117
38. C. J. Cramer, D. G. Truhlar, Chem. Rev. 1999, 99, 2161
39. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3093
40. J. Mosnacek, M. Bertoldo, C. Kosa, C. Cappelli, G. Ruggeri, I. Lukac, F. Ciardelli, Polym. Degrad. Stab. 2007, 92, 849-858
41. A. Klamt, WIREs Comput. Mol. Sci. 2011, 1, 699-709
42. J. Tomasi, WIREs Comput. Mol. Sci. 2011, 1, 855-867.
43. J. L. Rivail, D. Rinaldi, V. Dillet, Mol. Phys. 1996, 89, 1521-1529
44. C. Cappelli, in Continuum Solvation Models in Chemical Physics: Theory and Applications (Eds.:, B. Mennucci, R. Cammi,), Wiley, Chichester, 2007
45. B. Mennucci, C. Cappelli, C. A. Guido, R. Cammi, J. Tomasi, J. Phys. Chem. A 2009, 113, 3009-3020
46. A. V. Marenich, C. J. Cramer, D. G. Truhlar, C. A. Guido, B. Mennucci, G. Scalmani, M. Frisch, J. Chem. Sci. 2011, 2, 2143-2161.
47. Y. H. Wang, M. Halik, C. K. Wang, S. R. Marder, Y. Luo, J. Chem. Phys. 2005, 123, 194311
48. R. Improta, V. Barone, F. Santoro, Angew. Chem. 2007, 119, 409-412
49. Angew. Chem. Int. Ed. 2007, 46, 405-408
50. F. Avila Ferrer, R. Improta, F. Santoro, V. Barone, Phys. Chem. Chem. Phys. 2011, 13, 17007-17012.
51. A. Pucci, C. Cappelli, S. Bronco, G. Ruggeri, J. Phys. Chem. B 2006, 110, 3127-3134.
52. F. Donati, A. Pucci, C. Cappelli, B. Mennucci, G. Ruggeri, J. Phys. Chem. B 2008, 112, 3668-3679.
53. B. R. Crenshaw, C. Weder, Chem. Mater. 2003, 15, 4717-4724
54. C. Löwe, C. Weder, Adv. Mater. 2002, 14, 1625-1629.