Self-Assembly of Chiro-Optical Materials from Nonchiral Oligothiophene-Porphyrin Derivatives and Random Coil Synthetic Peptides
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
36173143
DOI
10.1002/cplu.202200262
Knihovny.cz E-zdroje
- Klíčová slova
- circular dichroism, oligothiophene, porphyrin, self-assembly, synthetic peptides,
- MeSH
- biomimetické materiály * MeSH
- mikroskopie elektronová rastrovací MeSH
- peptidy chemie MeSH
- porfyriny * chemie MeSH
- sekvence aminokyselin MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- peptidy MeSH
- porfyriny * MeSH
Biomimetic chiral optoelectronic materials can be utilized in electronic devices, biosensors and artificial enzymes. Herein, this work reports the chiro-optical properties and architectural arrangement of optoelectronic materials generated from self-assembly of initially nonchiral oligothiophene-porphyrin derivatives and random coil synthetic peptides. The photo-physical- and structural properties of the materials were assessed by absorption-, fluorescence- and circular dichroism spectroscopy, as well as dynamic light scattering, scanning electron microscopy and theoretical calculations. The materials display a three-dimensional ordered helical structure and optical activity that are observed due to an induced chirality of the optoelectronic element upon interaction with the peptide. Both these properties are influenced by the chemical composition of the oligothiophene-porphyrin derivative, as well as the peptide sequence. We foresee that our findings will aid in developing self-assembled optoelectronic materials with dynamic architectonical accuracies, as well as offer the possibility to generate the next generation of materials for a variety of bioelectronic applications.
Zobrazit více v PubMed
M. Lemaire, D. Delabouglise, R. Garreau, A. Guy, J. J. Roncali, Chem. Soc., Chem. Commun. 1988, 10, 658-661.
M. Andersson, P. O. Ekeblad, T, Hjertberg, O. Wennerström, O. Inganäs, Polym. Commun. 1991, 32, 546-548.
M. M. Bouman, E. W. Meijer, Adv. Mater. 1995, 7, 385-387.
G. Bidan, S. Guillerez, V. Sorokin, Adv. Mater. 1996, 8, 157-160.
F. Andreani, L. Angiolini, D. Caretta, E. Salatelli, J. Mater. Chem. 1998, 8, 1109-1111.
X. Huang, K. Nakanischi, N. Berova, Chirality 2000, 12, 237-255.
R. F. Pasternack, A. Giannetto, J. Am. Chem. Soc. 1991, 113, 7799-780.
P. C. Ewbank, G. Nuding, H. Suenaga, R. D. McCullough, S. Shinkai, Tetrahedron Lett. 2001, 42, 155-157.
H. A. Ho, M. Boissinot, M. G. Bergeron, G. Corbeil, K. Dore, D. Boudreau, M. Leclerc, Angew. Chem. Int. Ed. 2002, 41, 1548-1551;
Angew. Chem. 2002, 114, 1618-1621.
K. P. R. Nilsson, J. Rydberg, L. Baltzer, O. Inganäs, Proc. Natl. Acad. Sci. USA 2003, 100, 10170-10174.
K. P. R. Nilsson, J. Rydberg, L. Baltzer, O. Inganäs, Proc. Natl. Acad. Sci. USA 2004, 101, 11197-11202.
T. Sanji, N. Kato, M. Tanaka, Org. Lett. 2005, 8, 235-238.
J. R. Dunetz, C. Sandstrom, E. R. Young, P. Baker, S. A. Van Name, T. Cathopolous, R. Fairman, J. C. de Paula, K. S. Åkerfeldt, Org. Lett. 2005, 7, 2559-2561.
B. C. Kovaric, B. Kokona, A. D. Schwab, M. A. Twomey, J. C. de Paula, R. Fairman, J. Am. Chem. Soc. 2006, 128, 4166-4167.
A. Li, L. Zhao, J. Hao, R. Ma, Y. An, L. Shi, Langmuir 2014, 30, 4797-4805.
Y. Cao, Y. Duan, L. Han, S. Che, Chem. Commun. 2017, 53, 5641-5644.
R. Selegård, Z. Rouhbakhsh, H. Shirani, L. B. G. Johansson, P. Norman, M. Linares, D. Aili, K. P. R. Nilsson, Macromolecules 2017, 50, 7102-7110.
N. Kaerkitcha, T. Sagawa, Photochem. Photobiol. Sci. 2018, 17, 342-351.
R. J. Kumar, J. M. MacDonald, T. B. Singh, L. J. Waddington, A. B. Holmes, J. Am. Chem. Soc. 2011, 133, 8564-8573.
R. Matmour, I. De Cat, S. J. George, W. Adriaens, P. Leclère, P. H. H. Bomans, N. A. J. M. Sommerdijk, J. C. Gielen, P. C. M. Christianen, J. T. Heldens, J. C. M. van Hest, D. W. P. M. Löwik, S. De Feyter, E. W. Meijer, A. P. H. J. Schenning, J. Am. Chem. Soc. 2008, 130, 14576-14583.
S. R. Diegelmann, J. M. Gorham, J. D. Tovar, J. Am. Chem. Soc. 2008, 130, 13840-13841.
J. Deisenhofer, O. Epp, K. Miki, R. Huber, H. Michel, Nature 1985, 318, 618-624.
J. Barber, B. Andersson, Nature 1994, 370, 31-34.
J. Xiong, W. M. Fischer, K. Inoue, M. Nakahara, C. E. Bauer, Science 2000, 289, 1724-1730.
M. K. Panda, K. Ladomenou, A. G. Coutsolelos, Chem. Rev. 2012, 256, 2601-2627.
X.-S. Ke, B.-Y. Yang, X. Cheng, S. L.-F. Chan, J.-L. Zhang, Chem. Eur. J. 2014, 20, 4324-4333.
N. L. Bill, M. Ishida, Y. Kawashima, K. Ohkubo, Y. M. Sung, V. M. Lynch, J. M. Lim, D. Kim, J. L. Sessler, S. Fukuzumi, Chem. Sci. 2014, 5, 3888-3896.
T. Tanaka, A. Osuka, Chem. Soc. Rev. 2015, 44, 943-969.
J. Tang, J.-J. Chen, J. Jing, J.-Z. Chen, H. Lv, Y. Yu, P. Xu, J.-L. Zhang, Chem. Sci. 2014, 5, 558-566.
H. Lu, N. Kobayashi, Chem. Rev. 2016, 116, 6184-6261.
S. Olofsson, G. Johansson, L. Baltzer, J. Chem. Soc.-Perkin Trans. 1995, 2, 2047-2056.
L. Baltzer, H. Nilsson, J. Nilsson, Chem. Rev. (Washington, D.C.) 2001, 101, 3153-3163.
C. Aronsson, S. Danmark, F. Zhou, F. P. Öberg, K. Enander, H. Su, D. Aili, Sci. Rep. 2015, 5,14063.
S. Danmark, C. Aronsson, D. Aili, Biomacromolecules 2016, 17, 2260-2267.
K. Arja, M. Elgland, K. P. R. Nilsson, Front. Chem. 2018, 6, 391.
A. Åslund, C. J. Sigurdson, T. Klingstedt, S. Grathwohl, T. Bolmont, D. L. Dickstein, E. Glimsdal, S. Prokop, M. Lindgren, P. Konradsson, D. M. Holtzman, P. R. Hof, F. L. Heppner, S. Gandy, M. Jucker, A. Aguzzi, P. Hammarström, K. P. R. Nilsson, ACS Chem. Biol. 2009, 4, 673-684.
P. Sen, C. Hirel, C. Andraud, C. Aronica, Y. Bretonnière, A. Mohammed, H. Ågren, B. Minaev, V. Minaeva, G. Baryshnikov, H.-S. Lee, J. Duboisset, M. Lindgren, Materials (Basel) 2010, 3, 4446-4475.
B. Minaev, M. Lindgren, Sensors 2009, 9, 1937-1966.
B. M. W. Langeveld-Voss, R. A. J. Janssen, M. P. T. Christiaans, S. C. J. Meskers, H. P. J. M. Dekkers, E. W. Meijer, J. Am. Chem. Soc. 1996, 118, 4908-4909.
B. M. W. Langeveld-Voss, M. P. T. Christiaans, R. A. J. Janssen, E. W. Meijer, Macromolecules 1998, 31, 6702-6704.
Z. Rinkevicius, X. Li, O. Vahtras, K. Ahmadzadeh, M. Brand, M. Ringholm, N. H. List, M. Scheurer, M. Scott, A. Dreuw, P. Norman, WIREs Comput. Mol. Sci. 2020, 10, e1457.
M. Lindgren, P. Hammarström, FEBS J. 2010, 277, 1380-1388.
K. Arja, D. Sjölander, A. Åslund, S. Prokop, F. L. Heppner, P. Konradsson, M. Lindgren, P. Hammarström, K. O. A. Åslund, K. P. R. Nilsson, Macromol. Rapid Commun. 2013, 34, 723-730.
C. Gustafsson, H. Shirani, P. Leira, D. R. Rehn, M. Linares, P. Norman, M. Lindgren, ChemPhysChem 2021, 22, 323-335.
J. A. Maier, C. Martinez, K Kasavajhala, L. Wickstrom, K. E. Hauser, C. Simmerling, ff14SB: Improving the Accuracy of Protein Side Chain and Backbone Parameters from ff99SB. J. Chem. Theory Comput. 2015, 11, 3696-3713.
J. Wang, R. M. Wolf, J. W. Caldwell, P. A. Kollman, D. A. Case, J. Comput. Chem. 2004, 25, 1157-1174.
P. Li, K. M. Merz, J. Chem. Inf. Model. 2016, 56, 599-604.
J. Wang, P. Cieplak, P. A. Kollman, J. Comput. Chem. 2000, 21, 1049-1074.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, et al. Gaussian 16, 2016, Revision B.01.
D. Van der Spoel, E. Lindahl, B. Hess, G. Groenhof, A. E. Mark, H. J. C. Berendsen, J. Comput. Chem. 2005, 26, 1701-1718.
S. R. Durell, B. R. Brooks, A. Ben-Naim, J. Phys. Chem. 1994, 98, 2198-2202.
S. Nosé, J. Chem. Phys. 1984, 81, 511-519.
W. G. Hoover, Phys. Rev. A 1985, 31, 1695-1697.
M. Parrinello, A. Rahman, J. Appl. Phys. 1981, 52, 7182-7190.
T. Darden, D. York, L. Pedersen, J. Chem. Phys. 1993, 98, 10089-10092.
B. Hess, H. Bekker, H. J. C. Berendsen, J. G. E. M. Fraaije, J. Comput. Chem. 1997, 18, 1463-1472.
The PyMOL Molecular Graphics System, Version 1.8. 2015, Schrodinger, LLC.
Z. Rinkevicius, X. Li, O. Vahtras, K. Ahmadzadeh, M. Brand, M. Ringholm, N. Holmgaard List, M. Scheurer, M. Scott, A, Dreuw, P. Norman, Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2020, 10, e1457.