Towards Efficient and Photostable Red-Emitting Photonic Materials Based on Symmetric All-BODIPY-Triads, -Pentads, and -Hexads.
all-BODIPY multichromophores
energy transfer
lasers
photophysics
red-emitting materials
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 Nov 2019
22 Nov 2019
Historique:
received:
27
08
2019
pubmed:
14
9
2019
medline:
14
9
2019
entrez:
14
9
2019
Statut:
ppublish
Résumé
The development of efficient and stable red and near-IR emitting materials under hard radiation doses and/or prolonged times is a sought-after task due to their widespread applications in optoelectronics and biophotonics. To this aim, novel symmetric all-BODIPY-triads, -pentads, and -hexads have been designed and synthesized as light-harvesting arrays. These photonic materials are spectrally active in the 655-730 nm region and display high molar absorption across UV-visible region. Furthermore, they provide, to the best of our knowledge, the highest lasing efficiency (up to 68 %) and the highest photostability (tolerance >1300 GJ mol
Identifiants
pubmed: 31515840
doi: 10.1002/chem.201903804
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
14959-14971Subventions
Organisme : Ministerio de Economía, Industria y Competitividad, Gobierno de España
ID : CTQ2015-66702-R
Organisme : Ministerio de Economía, Industria y Competitividad, Gobierno de España
ID : MAT2017-83856-C3-1-P
Organisme : Ministerio de Economía, Industria y Competitividad, Gobierno de España
ID : MAT2017-83856-C3-3-P
Organisme : Ministerio de Ciencia, Innovación y Universidades
ID : RTI2018-094862-B-I00
Organisme : Osasun Saila, Eusko Jaurlaritzako
ID : IT912-16
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
M. Vendrell, D. Zhai, J. C. Er, Y. T. Chang, Chem. Rev. 2012, 112, 4391;
S. van de Linde, M. Sauer, Chem. Soc. Rev. 2014, 43, 1076;
A. J. C. Kuehne, M. C. Gather, Chem. Rev. 2016, 116, 12823;
P. Murto, A. Minotto, A. Zampetti, X. Xu, M. R. Andersson, F. Cacialli, E. Wang, Adv. Opt. Mater. 2016, 4, 2068;
Y. Zhang, S. Xia, M. fang, W. Mazi, Y. Zeng, T. Johnston, A. Pap, R. L. Luck, H. Liu, Chem. Commun. 2018, 54, 7625;
S. Zhu, Z. Rui, R. Tian, B. C. Yung, Q. Yang, S. Zhao, D. O. Kiesewetter, G. Niu, H. Sun, A. L. Antaris, X. Chen, Adv. Mater. 2018, 30, 1802546;
E. Oliveira, E. Bértolo, C. Nuñez, V. Pilla, H. M. Santos, J. Fernandez-Lodeiro, A. Fernandez-Lodeiro, J. Djafari, J. L. Capelo, C. Lodeiro, ChemistryOpen 2018, 7, 9;
C. Staudinger, J. Breininger, I. Klimant, S. M. Borisov, Analyst 2019, 144, 2393.
M. Grossi, M. Morgunova, S. Cheung, D. Scholz, E. Conroy, M. Terrile, A. Panarella, J. C. Simpson, W. M. Gallagher, D. F. O'Shea, Nat. Commun. 2016, 7, 10855;
X. Wu, Y. Zhang, K. Takle, O. Bilsel, Z. Li, H. Lee, Z. Zhang, D. Li, W. Fan, C. Duan, E. M. Chan, C. Lois, Y. Xiang, G. Han, ACS Nano 2016, 10, 1060;
J. Liu, Y.-Q. Sun, H. Zhang, H. Shi, Y. Shi, W. Guo, ACS Appl. Mater. Interfaces 2016, 8, 22953;
Y. Zhang, S. A. Autry, L. E. McNamara, S. T. Nguyen, N. Le, P. Brogdon, D. L. Watkins, N. I. Hammer, J. H. Delcamp, J. Org. Chem. 2017, 82, 5597;
D. Pfeifer, I. Klimant, S. M. Borisov, Chem. Eur. J. 2018, 24, 10711;
A. Adamow, L. Sznitko, E. Chrzumnicka, J. Stachera, A. Szukalski, T. Martynski, J. Mysliwiec, Sci. Rep. 2019, 9, 2143.
L. Yuan, W. Lin, K. Zheng, L. He, W. Huang, Chem. Soc. Rev. 2013, 42, 622;
Q. Zheng, M. F. Juette, S. Jockusch, M. R. Wassermann, Z. Zhou, R. B. Altman, S. C. Blanchard, Chem. Soc. Rev. 2014, 43, 1044;
Z. Yao, L. Yang, Y. Cai, C. Yan, M. Zhang, N. Cai, X. Dong, P. Wang, J. Phys. Chem. C 2014, 118, 2977;
A. Dessì, M. Calamante, A. Mordini, M. Peruzzini, A. Sinicropi, R. Basosi, F. Fabrizi, M. Taddei, D. Colonna, A. Di Carlo, G. Reginato, L. Zani, Chem. Commun. 2014, 50, 13952;
T. Kowada, H. Maeda, K. Kikuci, Chem. Soc. Rev. 2015, 44, 4953;
D. Wu, A. C. Sedgwick, T. Gunnalaugsson, E. U. Akkaya, J. Yoon, T. D. James, Chem. Soc. Rev. 2017, 46, 7105;
Z. Gao, Y. Hao, M. Zheng, Y. Chen, RSC Adv. 2017, 7, 7604;
C. Schwechheimer, F. Rönicke, U. Schepers, H. A. Wagenknecht, Chem. Sci. 2018, 9, 6557;
S. Basu, L. M. Needham, D. Lando, E. J. R. Taylor, K. J. Wohlfahrt, D. Shah, W. Boucher, Y. L. Tan, L. E. Bates, O. Takchenko, J. Cramard, B. C. Lagerholm, C. Eggeling, B. Hendrich, D. Klenerman, S. F. Lee, E. D. Laue, Nat. Commun. 2018, 9, 2520.
A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891;
G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. Int. Ed. 2008, 47, 1184;
Angew. Chem. 2008, 120, 1202;
R. Ziessel, G. Ulrich, A. Harriman, New J. Chem. 2007, 31, 496;
A. Treibs, F.-H. Kreuzer, Liebigs Ann. Chem. 1968, 718, 208-223.
A. Kamkaew, S. H. Lim, H. B. Lee, L. V. Kiew, L. Y. Chung, K. Burgess, Chem. Soc. Rev. 2013, 42, 77;
J. Fan, M. Hu, P. Zhan, X. Peng, Chem. Soc. Rev. 2013, 42, 29;
A. Bessette, G. S. Hanan, Chem. Soc. Rev. 2014, 43, 3342;
J. Zhao, J. K. Xu, W. Yang, Z. Wang, F. Zhong, Chem. Soc. Rev. 2015, 44, 8904;
Y. Ge, D. F. O'Shea, Chem. Soc. Rev. 2016, 45, 3846;
J. Bañuelos, Chem. Rec. 2016, 16, 355.
Y. Cakmak, E. U. Akkaya, Org. Lett. 2009, 11, 85;
V. Lakshmi, R. R. Rao, M. Ravikanth, Org. Biomol. Chem. 2015, 13, 2501;
N. Boens, B. Verbelen, W. Dehaen, Eur. J. Org. Chem. 2015, 6577;
C. F. A. Gómez-Durán, I. Esnal, I. Valois-Escamilla, A. Urias-Benavides, J. Bañuelos, I. Lopez Arbeloa, I. Garcia-Moreno, E. Peña-Cabrera, Chem. Eur. J. 2016, 22, 1048.
V. Lakshmi, R. Sharma, M. Ravikanth, Rep. Org. Chem. 2016, 6, 1;
H. Lu, J. Mack, Y. Yang, Z. Shen, Chem. Soc. Rev. 2014, 43, 4778.
I. J. Arroyo, R. Hu, G. Merino, B. Z. Tanag, E. Peña-Cabrera, J. Org. Chem. 2009, 74, 5719;
K. Tram, H. Yan, H. A. Jenkins, S. Vassiliev, D. Bruce, Dyes Pigm. 2009, 82, 392;
A. Schmitt, B. Hinkeldey, M. Wild, G. Jung, J. Fluoresc. 2009, 19, 755.
W. Wu, J. Zhao, H. Guo, J. Sun, S. Ji, Z. Wang, Chem. Eur. J. 2012, 18, 1961, (compound 3 a);
D. Zhang, Y. Wang, Y. Xiao, S. Qian, X. Qian, Tetrahedron 2009, 65, 8099, (compound 3 b).
L. Huang, X. Cui, B. Therrien, J. Zhao, Chem. Eur. J. 2013, 19, 17472.
W. Yang, A. Karatay, J. Zhao, J. Song, L. Zhao, Y. Xing, C. Zhang, C. He, H. G. Yaglioglu, M. Hayvali, A. Elmali, B. Küçüköz, Inorg. Chem. 2015, 54, 7492.
O. Buyukcakir, O. A. Bozdemir, S. Kolemen, S. Erbas, E. U. Akkaya, Org. Lett. 2009, 11, 4644;
D. Frath, J. Massue, G. Ulrich, R. Ziessel, Angew. Chem. Int. Ed. 2014, 53, 2290;
Angew. Chem. 2014, 126, 2322;
L. Jiao, Y. Wu, S. Wang, X. Hu, P. Zhang, C. Yu, K. Cong, Q. Meng, E. Hao, M. G. H. Vicent, J. Org. Chem. 2014, 79, 1830;
N. L. Bill, J. M. Lim, C. M. Davis, S. Bahring, J. O. Jeppesen, D. Kim, J. L. Sessler, Chem. Commun. 2014, 50, 6758;
C. Cheng, N. Gao, C. Yu, Z. Wang, J. Wang, E. Hao, Y. Wei, X. Mu, Y. Tian, C. Ran, L. Jian, Org. Lett. 2015, 17, 278.
S. P. Singh, T. Gayathri, Eur. J. Org. Chem. 2014, 4689;
L. Luo, D. Wu, W. Li, S. Zhang, Y. Ma, S. Yan, J. You, Org. Lett. 2014, 16, 6080;
C. Yu, L. Jiao, P. Zhang, Z. Feng, C. Cheng, Y. Wei, X. Mu, E. Hao, Org. Lett. 2014, 16, 3048;
S. Debnath, S. Singh, A. Bedi, K. Krishnamoorthy, S. S. Zade, J. Phys. Chem. C 2015, 119, 15859;
C. Maeda, T. Todaka, T. Ema, Org. Lett. 2015, 17, 3090;
S. Yamazawa, M. Nakashima, Y. Suda, R. Nishiyabu, Y. Kubo, J. Org. Chem. 2016, 81, 1310;
Z. Zhou, J. Zhou, L. Gai, A. Yuan, Z. Shen, Chem. Commun. 2017, 53, 6621;
A. Savoldelli, Q. Meng, R. Paolesse, F. R. Fronczek, K. M. Smith, M. G. H. Vicente, J. Org. Chem. 2018, 83, 6498;
Y. Li, Z. Qiao, T. Li, O. Zeika, K. Leo, ChemPhotoChem 2018, 2, 1017;
J. L. Belmonte-Vázquez, E. Avellanal-Zaballa, E. Enriquez-Palacios, L. Cerdan, I. Esnal, J. Bañuelos, C. Villegas-Gomez, I. Lopez-Arbeloa, E. Peña-Cabrera, J. Org. Chem. 2019, 84, 2523.
I. García-Moreno, D. Zhang, A. Costela, V. Martin, R. Sastre, Y. Xiao, J. Appl. Physiol. 2010, 107, 073105.
T. Bura, P. Retailleau, R. Ziessel, Angew. Chem. Int. Ed. 2010, 49, 6659;
Angew. Chem. 2010, 122, 6809;
Altan Bozdemir, S. Erbas-Cakmak, O. O. Ekiz, A. Dana, E. U. Akkaya, Angew. Chem. Int. Ed. 2011, 50, 10907;
Angew. Chem. 2011, 123, 11099;
R. Ziessel, G. Ulrich, A. Haefele, A. Harriman, J. Am. Chem. Soc. 2013, 135, 11330;
D. Su, J. Oh, S. C. Lee, J. M. Lim, S. Sahu, X. Yu, D. Kim, Y. T. Chang, Chem. Sci. 2014, 5, 4812;
M. A. H. Alamiry, A. Harriman, A. Haefele, R. Ziessel, ChemPhysChem 2015, 16, 1867;
A. Harriman, Chem. Commun. 2015, 51, 11745;
C. Azarias, R. Russo, L. Cupellini, B. Mennucci, D. Jacquemin, Phys. Chem. Chem. Phys. 2017, 19, 6443;
L. Lin, X. Lin, H. Guo, F. Yang, Org. Biomol. Chem. 2017, 15, 6006;
G. Reddy, N. Duvva, S. Seetharaman, F. D'Souza, L. Giribabu, Phys. Chem. Chem. Phys. 2018, 20, 27418.
L. Cerdán, E. Enciso, V. Martin, J. Bañuelos, I. Lopez-Arbeloa, A. Costela, I. Garcia-Moreno, Nat. Photonics 2012, 6, 621;
G. Duran-Sampedro, A. R. Agarrabeitia, I. Garcia-Moreno, L. Gartzia, S. de la Moya, J. Bañuelos, I. Lopez Arbeloa, M. J. Ortiz, Chem. Commun. 2015, 51, 11382;
E. Avellanal-Zaballa, G. Duran-Sampedro, A. Prieto-Castañeda, A. R. Agarrabeitia, I. Garcia-Moreno, I. Lopez-Arbeloa, J. Bañuelos, M. J. Ortiz, Phys. Chem. Chem. Phys. 2017, 19, 13210.
C. Y. Lee, O. K. Farha, B. J. Hong, A. A. Sarjeant, S. T. Nguyen, J. T. Hupp, J. Am. Chem. Soc. 2011, 133, 15858;
A. Meares, A. Satraitis, N. Santhanam, Z. Yu, M. Ptaszek, J. Org. Chem. 2015, 80, 3858;
G. Hu, R. Liu, E. J. Alexy, A. K. Mandal, D. F. Bocian, D. Holten, J. S. Lindsey, New J. Chem. 2016, 40, 8032;
M. D. Weber, V. Nikolaou, J. E. Wittmann, A. Nikolaou, P. A. Angaridis, G. Charalambidis, C. Stangel, A. Kahnt, A. G. Coutsolelos, R. D. Costa, Chem. Commun. 2016, 52, 1602;
A. N. Kursunlu, RSC Adv. 2014, 4, 47690;
H. R. A. Golf, A. M. Oltmanns, D. H. Trieu, H.-U. Reissig, A. Wiehe, Eur. J. Org. Chem. 2015, 4224.
S. Guo, L. Ma, J. Zhao, B. Kucukoz, A. Karatay, M. Hayvali, H. G. Yaglioglu, A. Elmali, Chem. Sci. 2014, 5, 489;
V. Bandi, F. P. D'Souza, H. B. Gobeze, F. D'Souza, Chem. Eur. J. 2015, 21, 2669;
S. Kumar, H. Gobeze, T. Chatterje, F. D'Souza, M. Ravikanth, J. Phys. Chem. A 2015, 119, 8338;
S. Kumar, K. G. Thorat, M. Ravikanth, J. Org. Chem. 2017, 82, 6568.
M. Galletta, F. Puntoriero, S. Campagna, C. Chiorboli, M. Quesada, S. Goeb, R. Ziessel, J. Phys. Chem. A 2006, 110, 4348;
J. Bañuelos, F. Lopez-Arbeloa, T. Arbeloa, S. Salleres, F. Amat-Guerri, M. Liras, I. Lopez-Arbeloa, J. Phys. Chem. A 2008, 112, 10822;
C. Dumas-Verdes, F. Miomandre, E. Lepicier, O. Galangau, T. T. Vu, G. Clavier, R. Meallet-Renault, P. Audebert, Eur. J. Org. Chem. 2010, 2525;
F. Puntoriero, F. Nastasi, S. Campagna, T. Bura, R. Ziessel, Chem. Eur. J. 2010, 16, 8832;
M. T. Whited, P. I. Djurovich, S. T. Roberts, A. C. Durrell, C. W. Schlenker, S. E. Bradforth, M. E. Thompson, J. Am. Chem. Soc. 2011, 133, 88;
T. Lazarides, S. Kuhri, G. Charalambidis, M. K. Panda, D. M. Guldi, A. G. Coutsolelos, Inorg. Chem. 2012, 51, 4193;
Q. Huaulmé, E. Cece, A. Mirloup, R. Ziessel, Tetrahedron Lett. 2014, 55, 4953;
S. Diring, F. Puntoriero, F. Nastasi, S. Campagna, R. Ziessel, J. Am. Chem. Soc. 2009, 131, 6108;
J. Iehl, J.-F. Nierengarten, A. Harriman, T. Bura, R. Ziessel, J. Am. Chem. Soc. 2012, 134, 988;
T. Bura, F. Nastasi, F. Puntoriero, S. Campagna, R. Ziessel, Chem. Eur. J. 2013, 19, 8900;
L. Huang, X. Cui, B. Therrien, J. Zhao, Chem. Eur. J. 2013, 19, 17472.
All-BODIPY based systems have been studied:
X. Zhang, Y. Xiao, X. Qian, Org. Lett. 2008, 10, 29;
G. Barin, M. D. Yilmaz, E. U. Akkaya, Tetrahedron Lett. 2009, 50, 1738;
O. A. Bozdemir, Y. Cakmak, F. Sozmen, T. Odzemir, A. Siemiarczuk, E. U. Akkaya, Chem. Eur. J. 2010, 16, 6346;
Y. Xiao, D. Zhang, X. Qian, A. Costela, I. Garcia-Moreno, V. Martin, M. E. Perez-Ojeda, J. Bañuelos, L. Garztia, I. Lopez-Arbeloa, Chem. Commun. 2011, 47, 11513;
P. Bonaccorsi, M. C. Aversa, A. Baratucci, T. Papalia, F. Puntoriero, S. Campagna, Chem. Commun. 2012, 48, 10550;
T. M. Khan, M. S. Shaik, M. Ravikanth, Dyes Pigm. 2012, 94, 66;
R. Sharma, H. B. Gobeze, F. D′Souza, M. Ravikanth, ChemPhysChem 2016, 17, 2516.
S. K. Mamidyala, M. G. Finn, Chem. Soc. Rev. 2010, 39, 1252;
M. Galibert, P. Dumy, D. Boturyn, Angew. Chem. Int. Ed. 2009, 48, 2576;
Angew. Chem. 2009, 121, 2614;
M. Meldal, C. W. Tornoe, Chem. Rev. 2008, 108, 2952.
J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249.
M. R. Martinez-Gonzalez, A. Urías-Benavides, E. Alvarado-Martínez, J. C. Lopez, A. M. Gómez, M. del Rio, I. Garcia, A. Costela, J. Bañuelos, T. Arbeloa, I. Lopez Arbeloa, E. Peña-Cabrera, Eur. J. Org. Chem. 2014, 5659;
M. L. Lepage, A. Mirloup, M. Ripoll, F. Stauffert, A. Bodlenner, R. Ziessel, P. Compain, Beilstein J. Org. Chem. 2015, 11, 659-667.
Styryl-BODIPY derivatives have proven to be remarkable near-IR emitting fluorophores.: for the first example of a monostyryl BODIPY, see:
K. Rurack, M. Kollmannsberger, J. Daub, Angew. Chem. Int. Ed. 2001, 40, 385;
Angew. Chem. 2001, 113, 396;
for the first example of a distyryl BODIPY see: Z. Dost, S. Atilgan, E. U. Akkaya, Tetrahedron 2006, 62, 8484.
J. Cristóbal López, M. del Rio, A. Oliden, J. Bañuelos, I. Lopez-Arbeloa, I. Garcia-Moreno, A. M. Gomez, Chem. Eur. J. 2017, 23, 17511.
M. del Río, F. Lobo, J. C. Lopez, A. Oliden, J. Bañuelos, I. Lopez-Arbeloa, I. Garcia-Moreno, A. M. Gomez, J. Org. Chem. 2017, 82, 1240.
E. Deniz, G. C. Isbasar, O. A. Bozdemir, L. T. Yildirim, A. Siemiarczuk, E. U. Akkaya, Org. Lett. 2008, 10, 3401.
A seminal approach to all-BODIPY chromophores based on the chemoselective Knoevenagel condensation of a pivotal formyl 4,4′-dialkynylboron BODIPY dye with 8-aryl-1,3,5,7-tetramethyl BODIPY derivatives had been described by Ziessel's group. In this process, the selectivity of the “crossed” condensation over the “self-Knoevenagel condensation” had been ascribed to a reactivity-reduction of the C-3, C-5 methyl groups in the former, induced by the steric congestion around the boron center, see reference [15a] and also: A. Mirloup, P. Retailleau, R. Ziessel, Tetrahedron Lett. 2013, 54, 4456.
M. Kitamura, T. Koga, M. Yano, T. Okauchi, Synlett 2012, 23, 1335.
L. Cerdán, A. Costela, I. García-Moreno, J. Bañuelos, I. López Arbeloa, Laser Phys. Lett. 2012, 9, 426.
Gaussian 16, Revision C.01, 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. V. 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. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. 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.