Please do not adjust margins
Organic & Biomolecular Chemistry
Page 5 of 7
DOI: 10.1039/C8OB01118D
Journal Name
Paper
electrochemical, spectroscopic and computational analyses
showed that in the neutral state CTTV exists in the “sofa”
conformation and upon oxidation undergoes interconversion
into a “boat” conformation where a pair of cofacially-arrayed
veratrole rings effectively stabilizes cationic charge via charge-
resonance.
14. D. Wang, M. R. Talipov, M. V. Ivanov, S. Mirzaei, S. V.
Lindeman, S. Cai, R. Rathore and S. A. Reid, The Journal of
Physical Chemistry Letters, 2018, 9, 4233-4238.
15. Y. Liu, S. Yan, J. Li and H. Shan, Polym. Bull. (Heidelberg,
Ger.), 2018, 75, 3667-3678.
16. E. Al-Farhan, P. M. Keehn and R. Stevenson, Tetrahedron
Lett., 1992, 33, 3591-3594.
We further examined the electron donor-acceptor (EDA)
complexes of CTTV with CA and DDQ using optical
spectroscopy and X-ray crystallography. In the solid state,
CTTV exists in a “sofa” conformation that is stabilized by the
charge-transfer interaction with four and two acceptor
molecules of CA and DDQ, respectively. We believe that these
findings can be applied to the design and synthesis of novel
organic functional molecules based on oxidation-induced
mechanical actuation.
17. V. Percec, C. G. Cho and C. Pugh, Macromolecules, 1991, 24
,
3227-3234.
18. B. Umezawa, O. Hoshino, H. Hara, K. Ohyama, S.
Mitsubayashi and J. Sakakibara, Chem. Pharm. Bull., 1969, 17
,
2240-2244.
19. J. D. White and B. D. Gesner, Tetrahedron Lett., 1968, 1591-
1594.
20. M. Martinez, F. L. Ochoa, R. Cruz-Almanza and R. A. Toscano,
J. Chem. Crystallogr., 1996, 26, 451-456.
Conflicts of interest
21. H. Zhang, J. W. Steed and J. L. Atwood, Supramol Chem,
There are no conflicts to declare.
1994, 4, 185-190.
22. A. Maliniak, Z. Luz, R. Poupko, C. Krieger and H.
Zimmermann, J. Am. Chem. Soc., 1990, 112, 4277-4283.
Acknowledgements
23. N. E. Burlinson and J. A. Ripmeester, J. Inclusion Phenom.,
We thank the NSF (CHE-1508677) for financial support and
Professor Scott A. Reid (Marquette University) for helpful
discussions. The calculations were performed on the high-
performance computing cluster Père at Marquette University
and XSEDE.
1985, 3, 95-98.
24. A. J. Cohen, P. Mori-Sánchez and W. Yang, Chem Rev, 2012,
112, 289-320.
25. S. Ehrlich, J. Moellmann and S. Grimme, Accounts Chem Res,
2013, 46, 916-926.
Notes and references
26. J. L. Bao, L. Gagliardi and D. G. Truhlar, The Journal of
Physical Chemistry Letters, 2018, 9, 2353-2358.
1. T. S. Navale, M. R. Talipov, R. Shukla and R. Rathore, J Phys
Chem C, 2016, 120, 19558-19565.
27. M. Renz, K. Theilacker, C. Lambert and M. Kaupp, J Am Chem
Soc, 2009, 131, 16292-16302.
2. K. Iwaso, Y. Takashima, A. Harada and A. Harada, Nat Chem,
28. F. Jensen, Chem Phys Lett, 1996, 261, 633-636.
2016, 8, 625-632.
29. M. R. Talipov, A. Boddeda, Q. K. Timerghazin and R. Rathore,
The Journal of Physical Chemistry C, 2014, 118, 21400-21408.
30. M. V. Ivanov, D. Wang, S. H. Wadumethridge and R. Rathore,
3. S. C. Everhart, U. K. Jayasundara, H. Kim, R. Procupez-
Schtirbu, W. A. Stanbery, C. H. Mishler, B. J. Frost, J. I. Cline, T.
W. Bell and R. Procupez-Schtirbu, Chemistry, 2016, 22, 11291-
11302.
The Journal of Physical Chemistry Letters, 2017,
8, 4226-4230.
31. D. Kokkin, M. V. Ivanov, J. Loman, J.-Z. Cai, R. Rathore and S.
4. H. J. Shepherd, I. y. A. Gural'skiy, C. M. Quintero, S. Tricard, L.
A. Reid, The Journal of Physical Chemistry Letters, 2018, 9, 2058-
Salmon, G. Molnar and A. Bousseksou, Nat. Commun., 2013, 4,
2061.
2607.
32. M. R. Talipov and R. Rathore, in Organic Redox Systems, ed.
T. Nishinaga, 2015.
5. V. J. Chebny, R. Shukla, S. V. Lindeman and R. Rathore, Org.
Lett., 2009, 11, 1939-1942.
33. T. S. Navale, K. Thakur, V. S. Vyas, S. H. Wadumethrige, R.
Shukla, S. V. Lindeman and R. Rathore, Langmuir, 2012, 28, 71-
83.
6. C. Song and T. M. Swager, Org. Lett., 2008, 10, 3575-3578.
7. R. Rathore, V. J. Chebny, E. J. Kopatz and I. A. Guzei, Angew.
Chem., Int. Ed., 2005, 44, 2771-2774.
34. M. R. Talipov, A. Boddeda, M. M. Hossain and R. Rathore, J.
Phys. Org. Chem., 2016, 29, 227-233.
8. C. Li, N. Gunari, K. Fischer, A. Janshoff and M. Schmidt,
Angew. Chem., Int. Ed., 2004, 43, 1101-1104.
35. R. Rathore, S. V. Lindeman and J. K. Kochi, J Am Chem Soc,
1997, 119, 9393-9404.
9. B. Rout, L. Motiei and D. Margulies, Synlett, 2014, 25, 1050-
1054, 1055 pp.
36. J. K. Kochi, R. Rathore and P. Le Magueres, J. Org. Chem.,
2000, 65, 6826-6836.
10. I. Leray and B. Valeur, Eur. J. Inorg. Chem., 2009, 3525-3535.
11. D. Wang, M. V. Ivanov, D. Kokkin, J. Loman, J.-Z. Cai, S. A.
Reid and R. Rathore, Angew. Chem., Int. Ed., 2018, 57, 8189-
8193.
37. J.-M. Lue, S. V. Rosokha and J. K. Kochi, J. Am. Chem. Soc.,
2003, 125, 12161-12171.
38. H. A. Benesi and J. H. Hildebrand, J Am Chem Soc, 1949, 71
,
12. P. A. Pieniazek, A. I. Krylov and S. E. Bradforth, The Journal of
Chemical Physics, 2007, 127, 044317.
2703-2707.
39. S. V. Lindeman, J. Hecht and J. K. Kochi, J. Am. Chem. Soc.,
2003, 125, 11597-11606.
13. R. Shukla, K. Thakur, V. J. Chebny, S. A. Reid and R. Rathore,
J. Phys. Chem. B, 2010, 114, 14592-14595.
40. A. S. Jalilov, J. Lu and J. K. Kochi, J. Phys. Org. Chem., 2016,
29, 35-41.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins