Halogen-Bonded BODIPY Frameworks with Tunable Optical Features*
Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
PubMed
32996613
DOI
10.1002/chem.202003945
Knihovny.cz E-zdroje
- Klíčová slova
- BODIPY, fluorescence enhancement, halogen bonding, solid-state assemblies, tunable optical features,
- Publikační typ
- časopisecké články MeSH
The ability to tune the optical features of BODIPY materials in the solid state is essential for their photorelated application and requires efficient control of the crystal packing. In this study, such control of BODIPY supramolecular assemblies was achieved by deliberate design and synthesis of a BODIPY containing a strong halogen-bond (XB) acceptor (-NO2 ) and donor (I, Br) to mediate XB interactions. The di-halogenated structures formed isostructural mono-coordinate motif B3, B4 (1D tubular structure) and symmetric bifurcated motif B4-II (1D zigzag chains structure) through N-O⋅⋅⋅I, Br XB interactions. These XB interactions promote singlet-to-triplet intersystem crossing and triplet-to-singlet reverse intersystem crossing due to partial delocalization of oxygen electrons onto Br and I, which leads to unexpected fluorescence enhancement of B4-II. Finally, the indirect optical band gaps of B3, B4 and B4-II were amenable to tuning in the range of 1.85-2.50 eV by XB-driven crystal packings.
Department of Chemistry Faculty of Science Gebze Technical University 41400 Gebze Kocaeli Turkey
Department of Physics Faculty of Science Gebze Technical University 41400 Gebze Kocaeli Turkey
Zobrazit více v PubMed
S. P. Singh, T. Gayathri, Eur. J. Org. Chem. 2014, 4689-4707.
H. Usta, M. D. Yilmaz, A. J. Avestro, D. Boudinet, M. Denti, W. Zhao, J. F. Stoddart, A. Facchetti, Adv. Mater. 2013, 25, 4327-4334.
N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 2012, 41, 1130-1172.
H. He, L. Si, Y. Zhong, M. Dubey, Chem. Commun. 2012, 48, 1886-1888.
T. Zhang, X. Zhu, W. K. Wong, H. L. Tam, W. Y. Wong, Chem. Eur. J. 2013, 19, 739-748.
Z. Liu, Z. Jiang, M. Yan, X. Wang, Front. Chem. 2019, 7, 1-16.
M. Yamaguchi, S. Ito, A. Hirose, K. Tanaka, Y. Chujo, Mater. Chem. Front. 2017, 1, 1573-1579.
C. L. Liu, Y. Chen, D. P. Shelar, C. Li, G. Cheng, W. F. Fu, J. Mater. Chem. C 2014, 2, 5471-5478.
S. Kim, J. Bouffard, Y. Kim, Chem. Eur. J. 2015, 21, 17459-17465.
G. Fan, Y. X. Lin, L. Yang, F. P. Gao, Y. X. Zhao, Z. Y. Qiao, Q. Zhao, Y. S. Fan, Z. Chen, H. Wang, Chem. Commun. 2015, 51, 12447-12450.
C. Spies, A. M. Huynh, V. Huch, G. Jung, J. Phys. Chem. C 2013, 117, 18163-18169.
S. Choi, J. Bouffard, Y. Kim, Chem. Sci. 2014, 5, 751-755.
D. Tian, F. Qi, H. Ma, X. Wang, Y. Pan, R. Chen, Z. Shen, Z. Liu, L. Huang, W. Huang, Nat. Commun. 2018, 9, 1-9.
P. Metrangolo, C. Präsang, G. Resnati, R. Liantonio, A. C. Whitwood, D. W. Bruce, Chem. Commun. 2006, 3290-3292.
P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. Int. Ed. 2008, 47, 6114-6127;
Angew. Chem. 2008, 120, 6206-6220.
J. Cao, X. Yan, W. He, X. Li, Z. Li, Y. Mo, M. Liu, Y. B. Jiang, J. Am. Chem. Soc. 2017, 139, 6605-6610.
J. Dahlke, R. Tepper, R. Geitner, S. Zechel, J. Vitz, R. Kampes, J. Popp, M. D. Hager, U. S. Schubert, Polym. Chem. 2018, 9, 2193-2197.
M. Saccone, G. Cavallo, P. Metrangolo, G. Resnati, A. Priimagi, Top. Curr. Chem. 2014, 359, 147-166.
P. Auffinger, F. A. Hays, E. Westhof, P. S. Ho, Proc. Natl. Acad. Sci. USA 2004, 101, 16789-16794.
L. C. Gilday, S. W. Robinson, T. A. Barendt, M. J. Langton, B. R. Mullaney, P. D. Beer, Chem. Rev. 2015, 115, 7118-7195.
Y. Lee, R. M. Malamakal, D. M. Chenoweth, J. M. Anna, J. Phys. Chem. Lett. 2020, 11, 877-884.
O. Bolton, K. Lee, H. J. Kim, K. Y. Lin, J. Kim, Nat. Chem. 2011, 3, 205-210.
J. K. Salunke, N. A. Durandin, T. P. Ruoko, N. R. Candeias, P. Vivo, E. Vuorimaa-Laukkanen, T. Laaksonen, A. Priimagi, Sci. Rep. 2018, 8, 1-8.
S. J. Ang, T. S. Chwee, M. W. Wong, J. Phys. Chem. C 2018, 122, 12441-12447.
D. Yan, A. Delori, G. O. Lloyd, T. Friščić, G. M. Day, W. Jones, J. Lu, M. Wei, D. G. Evans, X. Duan, Angew. Chem. Int. Ed. 2011, 50, 12483-12486;
Angew. Chem. 2011, 123, 12691-12694.
L. Xiao, Y. Wu, Z. Yu, Z. Xu, J. Li, Y. Liu, J. Yao, H. Fu, Chem. Eur. J. 2018, 24, 1801-1805.
V. Kumar, T. Pilati, G. Terraneo, F. Meyer, P. Metrangolo, G. Resnati, Chem. Sci. 2017, 8, 1801-1810.
M. Gorbe, A. M. Costero, F. Sancenón, R. Martínez-Máñez, R. Ballesteros-Cillero, L. E. Ochando, K. Chulvi, R. Gotor, S. Gil, Dye Pigment. 2019, 160, 198-207.
M. I. Martinez Espinoza, L. Sori, A. Pizzi, G. Terraneo, I. Moggio, E. Arias, G. Pozzi, S. Orlandi, V. Dichiarante, P. Metrangolo, M. Cavazzini, F. Baldelli Bombelli, Chem. Eur. J. 2019, 25, 9078-9087.
M. Su, X. Yan, X. Guo, Q. Li, Y. Zhang, C. Li, Chem. Eur. J. 2020, 26, 4505-4509.
H. Hassanain, E. S. Davies, W. Lewis, D. L. Kays, N. R. Champness, Crystals 2020, 10, 36.
Gaussian 09, Revision A.02, M. J. Frisch, G W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian, Inc., Wallingford CT, 2016.
J. F. Gonthier, S. N. Steinmann, L. Roch, A. Ruggi, N. Luisier, K. Severin, C. Corminboeuf, Chem. Commun. 2012, 48, 9239-9241.
B. Jeziorski, R. Moszynski, K. Szalewicz, Chem. Rev. 1994, 94, 1887-1930.
T. Korona, R. Moszynski, B. Jeziorski, J. Chem. Phys. 1996, 105, 8178-8186.
K. Szalewicz, Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 254-272.
N. R. Goud, O. Bolton, E. C. Burgess, A. J. Matzger, Cryst. Growth Des. 2016, 16, 1765-1771.
S. Tothadi, P. Sanphui, G. R. Desiraju, Cryst. Growth Des. 2014, 14, 5293-5302.
J. C. Bennion, L. Vogt, M. E. Tuckerman, A. J. Matzger, Cryst. Growth Des. 2016, 16, 4688-4693.
A. Ebrahimi, H. Razmazma, H. S. Delarami, Res. Lett. Phys. Chem. 2016, 4, 1-15.
X. Ma, K. Cai, J. Wang, J. Phys. Chem. B 2011, 115, 1175-1187.
Q. Jin Shen, W. Jun Jin, Phys. Chem. Chem. Phys. 2011, 13, 13721-13729.
J. Karolin, L. B. A. Johansson, L. Strandberg, T. Ny, J. Am. Chem. Soc. 1994, 116, 7801-7806.
A. Gorman, J. Killoran, C. O'Shea, T. Kenna, W. M. Gallagher, D. F. O'Shea, J. Am. Chem. Soc. 2004, 126, 10619-10631.
X. Miao, W. Hu, T. He, H. Tao, Q. Wang, R. Chen, L. Jin, H. Zhao, X. Lu, Q. Fan, W. Huang, Chem. Sci. 2019, 10, 3096-3102.
Q. J. Hu, Y. C. Lu, C. X. Yang, X. P. Yan, Chem. Commun. 2016, 52, 5470-5473.
J. Tauc, R. Grigorovici, A. Vancu, Phys. Stat. Sol. 1966, 15, 625-627.
J. Tauc, Optical Properties of Solids, Abeles, North Holland, Amsterdam, 1972.
N. F. Mott, E. A. Davis, Philos. Mag. 1970, 22, 7.
