Oxacycle-Fused [1]Benzothieno[3,2-b][1]benzothiophene Derivatives: Synthesis, Electronic Structure, Electrochemical Properties, Ionisation Potential, and Crystal Structure.
arenes
crystal engineering
electrochemistry
electronic properties
π-conjugation
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
09 2019
09 2019
Historique:
received:
04
07
2018
entrez:
17
1
2020
pubmed:
17
1
2020
medline:
17
1
2020
Statut:
ppublish
Résumé
The molecular properties of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) are vulnerable to structural modifications, which in turn are determined by the functionalization of the backbone. Hence versatile synthetic strategies are needed to discover the properties of this molecule. To address this, we have attempted heteroatom (oxygen) functionalization of BTBT by a concise and easily scalable synthesis. Fourfold hydroxy-substituted BTBT is the key intermediate, from which the compounds 2,3,7,8-bis(ethylenedioxy)-[1]benzothieno[3,2-b][1]benzothiophene and 2,3,7,8-bis(methylenedioxy)-[1]benzothieno[3,2-b][1]benzothiophene are synthesized. The difference in ether functionalities on the BTBT scaffold influences the ionisation potential values substantially. The crystal structure reveals the transformation of the herringbone motif in bare BTBT towards π-stacked columns in the newly synthesized derivatives. The results are further justified by the simulated HOMO levels of the model compound.
Identifiants
pubmed: 31944036
doi: 10.1002/cplu.201800346
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1263-1269Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
K. Takimiya, S. Shinamura, I. Osaka, E. Miyazaki, Adv. Mater. 2011, 23, 4347-4370;
H. Sirringhaus, Adv. Mater. 2014, 26, 1319-1335;
J. H. Gao, R. J. Li, L. Q. Li, Q. Meng, H. Jiang, H. X. Li, W. P. Hu, Adv. Mater. 2007, 19, 3008-3011;
R. Li, L. Jiang, Q. Meng, J. Gao, H. Li, Q. Tang, M. He, W. Hu, Y. Liu, D. Zhu, Adv. Mater. 2009, 21, 4492-4495;
Y. Miyata, E. Yoshikawa, T. Minari, K. Tsukagoshi, S. Yamaguchi, J. Mater. Chem. 2012, 22, 7715-7717;
K. Xiao, Y. Liu, T. Qi, W. Zhang, F. Wang, J. Gao, W. Qiu, Y. Ma, G. Cui, S. Chen, X. Zhan, G. Yu, J. Qin, W. Hu, D. Zhu, J. Am. Chem. Soc. 2005, 127, 13281-13286;
K. Takimiya, H. Ebata, K. Sakamoto, T. Izawa, T. Otsubo, Y. Kunugi, J. Am. Chem. Soc. 2006, 128, 12604-12605.
K. Takimiya, I. Osaka, T. Mori, M. Nakano, Acc. Chem. Res. 2014, 47, 1493-1502.
V. S. Vyas, R. Gutzler, J. Nuss, K. Kern, B. V. Lotsch, CrystEngComm 2014, 16, 7389-7392.
S. Haruki, Y. Syuji, J. Heterocycl. Chem. 1998, 35, 725-726;
M. Saito, T. Yamamoto, I. Osaka, E. Miyazaki, K. Takimiya, H. Kuwabara, M. Ikeda, Tetrahedron Lett. 2010, 51, 5277-5280;
M. Saito, I. Osaka, E. Miyazaki, K. Takimiya, H. Kuwabara, M. Ikeda, Tetrahedron Lett. 2011, 52, 285-288.
H. Ebata, T. Izawa, E. Miyazaki, K. Takimiya, M. Ikeda, H. Kuwabara, T. Yui, J. Am. Chem. Soc. 2007, 129, 15732-15733;
C. Liu, T. Minari, X. Lu, A. Kumatani, K. Takimiya, K. Tsukagoshi, Adv. Mater. 2011, 23, 523-526.
G. Schweicher, V. Lemaur, C. Niebel, C. Ruzie, Y. Diao, O. Goto, W. Y. Lee, Y. Kim, J. B. Arlin, J. Karpinska, A. R. Kennedy, S. R. Parkin, Y. Olivier, S. C. Mannsfeld, J. Cornil, Y. H. Geerts, Z. Bao, Adv. Mater. 2015, 27, 3066-3072;
H. Iino, T. Usui, J. Hanna, Nat. Commun. 2015, 6, 6828.
C. Ruzie, J. Karpinska, A. R. Kennedy, Y. H. Geerts, J. Org. Chem. 2013, 78, 7741-7748.
K. Takimiya, H. Kuwahara, T. Yui, M. Ikeda, JP2010001236 A (Hiroshima University, Japan), 2010;
A. Wigglesworth, Y. Wu, P. Liu, M. A. Heuft, CA2762471 A1 (Xerox Corporation, USA), 2012;
M. Nakatsuka, JP2011258900 A (Yamamoto Chemicals Inc., Japan), 2011;
K. Kobayashi, K. Kimura, T. Susuki, H. Satou, Y. Tani, WO2010050575 A1 (FujiFilm Corporation, Japan), 2010;
M. Nakatsuka, JP2009021390 A (Yamamoto Chemicals Inc., Japan), 2009;
K. Takimiya, S. Shinamura, M. Hamada, Y. Sadamitsu, WO2014030700 A1 (Nippon Kayaku Kabushiki Kaisha, Japan), 2014.
G. Gryn′ova, C. Corminboeuf, J. Phys. Chem. Lett. 2016, 7, 5198-5204.
L. Yan, Y. Zhao, H. Yu, Z. Hu, Y. He, A. Li, O. Goto, C. Yan, T. Chen, R. Chen, Y.-L. Loo, D. F. Perepichka, H. Meng, W. Huang, J. Mater. Chem. C 2016, 4, 3517-3522;
L. Yifan, G. o. Ganna, S. Felipe, J. Xavier, S. Kevin, C. Clémence, W. Jérôme, Chem. Eur. J. 2017, 23, 8058-8065;
C. Wang, H. Nakamura, H. Sugino, K. Takimiya, J. Mater. Chem. C 2018, 6, 3604-3612.
M. Matsumura, A. Muranaka, R. Kurihara, M. Kanai, K. Yoshida, N. Kakusawa, D. Hashizume, M. Uchiyama, S. Yasuike, Tetrahedron 2016, 72, 8085-8090.
X. Cheng, Y.-Y. Noh, J. Wang, M. Tello, J. Frisch, R.-P. Blum, A. Vollmer, J. P. Rabe, N. Koch, H. Sirringhaus, Adv. Funct. Mater. 2009, 19, 2407-2415.
M. M. Payne, J. H. Delcamp, S. R. Parkin, J. E. Anthony, Org. Lett. 2004, 6, 1609-1612;
J. Hellberg, E. Dahlstedt, M. E. Pelcman, Tetrahedron 2004, 60, 8899-8912;
J. E. Anthony, J. Gierschner, C. A. Landis, S. R. Parkin, J. B. Sherman, R. C. Bakus Ii, Chem. Commun. 2007, 4746-4748;
O. L. Griffith, J. E. Anthony, A. G. Jones, Y. Shu, D. L. Lichtenberger, J. Am. Chem. Soc. 2012, 134, 14185-14194;
M. J. Bruzek, J. E. Anthony, Org. Lett. 2014, 16, 3608-3610;
H. Mori, X. C. Chen, N. H. Chang, S. Hamao, Y. Kubozono, K. Nakajima, Y. Nishihara, J. Org. Chem. 2014, 79, 4973-4983.
T. Higashino, A. Ueda, J. Yoshida, H. Mori, Chem. Commun. 2017, 53, 3426-3429.
J. H. Clark, H. L. Holland, J. M. Miller, Tetrahedron Lett. 1976, 17, 3361-3364.
G. Christine, L. Claudia, L. Shi-Xia, S. Lionel, L. Eric, H. Andreas, D. Silvio, ChemPhysChem 2007, 8, 1504-1512;
S. Bouguessa, K. Herve, S. Golhen, L. Ouahab, J.-M. Fabre, New J. Chem. 2003, 27, 560-564.
Y. Tsutsui, G. Schweicher, B. Chattopadhyay, T. Sakurai, J. B. Arlin, C. Ruzie, A. Aliev, A. Ciesielski, S. Colella, A. R. Kennedy, V. Lemaur, Y. Olivier, R. Hadji, L. Sanguinet, F. Castet, S. Osella, D. Dudenko, D. Beljonne, J. Cornil, P. Samori, S. Seki, Y. H. Geerts, Adv. Mater. 2016, 28, 7106-7114.
C. Ruzie, J. Karpinska, A. Laurent, L. Sanguinet, S. Hunter, T. D. Anthopoulos, V. Lemaur, J. Cornil, A. R. Kennedy, O. Fenwick, P. Samori, G. Schweicher, B. Chattopadhyay, Y. H. Geerts, J. Mater. Chem. C 2016, 4, 4863-4879.
C. Niebel, Y. Kim, C. Ruzie, J. Karpinska, B. Chattopadhyay, G. Schweicher, A. Richard, V. Lemaur, Y. Olivier, J. Cornil, A. R. Kennedy, Y. Diao, W.-Y. Lee, S. Mannsfeld, Z. Bao, Y. H. Geerts, J. Mater. Chem. C 2015, 3, 674-685.
T. Yamamoto, T. Nishimura, T. Mori, E. Miyazaki, I. Osaka, K. Takimiya, Org. Lett. 2012, 14, 4914-4917.
B. A. Keay, H. P. Plaumann, D. Rajapaksa, R. Rodrigo, Can. J. Chem. 1983, 61, 1987-1995.
A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
G. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
M. A. Spackman, D. Jayatilaka, CrystEngComm 2009, 11, 19-32;
A. S. Mark, Phys. Scr. 2013, 87, 048103.
M. A. Spackman, J. J. McKinnon, CrystEngComm 2002, 4, 378-392.
M. J. Frisch, Gaussian 09 (Gaussian, Inc., Wallingford CT, 2009).
Y. Chen, B. Lee, H. T. Yi, S. S. Lee, M. M. Payne, S. Pola, C.-H. Kuo, Y.-L. Loo, J. E. Anthony, Y. T. Tao, V. Podzorov, Phys. Chem. Chem. Phys. 2012, 14, 14142-14151;
D. Choi, P.-H. Chu, M. McBride, E. Reichmanis, Chem. Mater. 2015, 27, 4167-4168.
E. G. Bittle, J. I. Basham, T. N. Jackson, O. D. Jurchescu, D. J. Gundlach, Nat. Commun. 2016, 7, 10908;
T. Uemura, C. Rolin, T.-H. Ke, P. Fesenko, J. Genoe, P. Heremans, J. Takeya, Adv. Mater. 2016, 28, 151-155;
I. McCulloch, A. Salleo, M. Chabinyc, Science 2016, 352, 1521-1522;
H. H. Choi, K. Cho, C. D. Frisbie, H. Sirringhaus, V. Podzorov, Nat. Mater. 2018, 17, 2-7.