Subscribe to RSS
DOI: 10.1055/s-0041-1725075
Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers
Funding Information This work was funded by the Australian Research Council through the ARC Centre of Excellence in Exciton Science (CE170100026).
Abstract
Oligo(p-phenylene)s with a donor phenol group and an acceptor pyridinium moiety separated by one and two p-phenylene units were synthesized by the linear iterative Suzuki–Miyaura coupling method using aryl nonaflates as effective coupling reagents. Zwitterionic forms of these push–pull molecules were generated upon deprotonation of the phenol leading to large redshifts in absorbance maxima. UV-vis absorbance studies also revealed strong dependence of the band position on solvent polarity: a smooth bathochromic shift can be observed with the decrease of the solvent polarity. The molecule with one p-phenylene bridging unit showed the strongest solvatochromic characteristics in the series, spanning the range of 167 nm while moving from polar water to less polar N,N-dimethylformamide. The magnitude of this shift was close to Reichardt's dye — one of the most solvatochromic organic dyes known.
Supporting Information
Supporting Information for this article is available online at https://doi.org/10.1055/s-0041-1725075.
Dedicated to Prof. Peter Bäuerle on his 65th birthday.
Publication History
Received: 15 January 2021
Accepted: 01 February 2021
Article published online:
01 April 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Fort A, Boeglin A, Mager L, Amyot C, Combellas C, Thiébault A, Rodriguez V. Synth. Met. 2001; 124: 209
- 2 Boeglin A, Fort A, Mager L, Combellas C, Thiébault A, Rodriguez V. Chem. Phys. 2002; 282: 353
- 3 Reichardt C. Chem. Rev. 1994; 94: 2319
- 4 He GS, Zhu J, Baev A, Samoć M, Frattarelli DL, Watanabe N, Facchetti A, Ågren H, Marks TJ, Prasad PN. J. Am. Chem. Soc. 2011; 133: 6675
- 5 Marder SR, Kippelen B, Jen AK.-Y, Peyghambarian N. Nature 1997; 388: 845
- 6 Diemer V, Chaumeil H, Defoin A, Fort A, Boeglin A, Carré C. Eur. J. Org. Chem. 2006; 2727
- 7 Shi Y, Frattarelli D, Watanabe N, Facchetti A, Cariati E, Righetto S, Tordin E, Zuccaccia C, Macchioni A, Wegener SL, Stern CL, Ratner MA, Marks TJ. J. Am. Chem. Soc. 2015; 137: 12521
- 8 Yamaguchi I, Yamaji R. J. Phys. Org. Chem. 2017; 30: e3671
- 9 Yamaguchi I, Goto K, Sato M. Tetrahedron 2009; 65: 3645
- 10 Brooker L, Keyes G, Heseltine D. J. Am. Chem. Soc. 1951; 73: 5350
- 11 Morley JO, Morley RM, Docherty R, Charlton MH. J. Am. Chem. Soc. 1997; 119: 10192
- 12 Rezende MC. J. Phys. Org. Chem. 2016; 29: 460
- 13 Catalan J, Mena E, Meutermans W, Elguero J. J. Phys. Chem. 1992; 96: 3615
- 14 Diemer V, Chaumeil H, Defoin A, Jacques P, Carré C. Tetrahedron Lett. 2005; 46: 4737
- 15 Machado VG, Stock RI, Reichardt C. Chem. Rev. 2014; 114: 10429
- 16 Robert F, Winum J.-Y, Sakai N, Gerard D, Matile S. Org. Lett. 2000; 2: 37
- 17 Martin RE, Diederich F. Angew. Chem. Int. Ed. 1999; 38: 1350
- 18 Arnaud-Neu F, Delgado R, Chaves S. Pure Appl. Chem. 2003; 75: 71
- 19 Li ZH, Wong MS, Tao Y, D'Iorio M. J. Org. Chem. 2004; 69: 921
- 20 Ahn K.-H, Ryu GY, Youn S.-W, Shin D.-M. Mater. Sci. Eng., C 2004; 24: 163
- 21 Cheng Y.-J, Luh T.-Y. J. Organomet. Chem. 2004; 689: 4137
- 22 Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
- 23 Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
- 24 Lennox AJ, Lloyd-Jones GC. Chem. Soc. Rev. 2014; 43: 412
- 25 Vogel MA, Stark CB, Lyapkalo IM. Synlett 2007; 2907
- 26 Hoegermeier J, Reißig HU. Chem. Eur. J. 2007; 13: 2410
- 27 Rottländer M, Knochel P. J. Org. Chem. 1998; 63: 203
- 28 Blettner CG, König WA, Stenzel W, Schotten T. J. Org. Chem. 1999; 64: 3885
- 29 Dominguez M, Reissig H.-U. Synthesis 2014; 46: 1100
- 30 Lou S, Fu GC. Adv. Synth. Catal. 2010; 352: 2081
- 31 Kudo N, Perseghini M, Fu GC. Angew. Chem. Int. Ed. 2006; 45: 1282
- 32 Lott RS, Chauhan VS, Stammer CH. J. Chem. Soc., Chem. Commun. 1979; 495
- 33 Sajiki H, Kuno H, Hirota K. Tetrahedron Lett. 1997; 38: 399
- 34 Sun Z, Zhou T, Pan X, Yang Y, Huan Y, Xiao Z, Shen Z, Liu Z. Bioorg. Med. Chem. Lett. 2018; 28: 3050
- 35 Chouhan M, Kumar K, Sharma R, Grover V, Nair VA. Tetrahedron Lett. 2013; 54: 4540
- 36 Greene TW. Greene's Protective Groups in Organic Synthesis, 5th ed. John Wiley & Sons, Inc.; Hoboken, New Jersey: 2014: 475
- 37 Bäuerle P, Würthner F, Heid S. Angew. Chem. Int. Ed. Engl. 1990; 29: 419
- 38 Chaumeil H, Neuburger M, Jacques P, Tschamber T, Diemer V, Carré C. Tetrahedron 2014; 70: 3116
- 39a X-ray crystallographic data for compound [OPP(2)-O−]2·HCl were deposited in the Cambridge Crystallographic Data Centre (CCDC) with identification number 2055376
- 39b X-ray crystallographic data for compound OPP(3)-OH were deposited in the Cambridge Crystallographic Data Centre (CCDC) with identification number 2055377
- 40 Jacques P, Graff B, Diemer V, Ay E, Chaumeil H, Carré C, Malval J.-P. Chem. Phys. Lett. 2012; 531: 242
- 41 Effenberger F, Wuerthner F, Steybe F. J. Org. Chem. 1995; 60: 2082
- 42 Würthner F, Yao S, Debaerdemaeker T, Wortmann R. J. Am. Chem. Soc. 2002; 124: 9431
- 43 Albert ID. L, Marks TJ, Ratner MA. J. Am. Chem. Soc. 1998; 120: 11174
- 44 Fabian J, Rosquete G, Montero-Cabrera L. J. Mol. Struct. THEOCHEM 1999; 469: 163
- 45 Pati SK, Marks TJ, Ratner MA. J. Am. Chem. Soc. 2001; 123: 7287
- 46 Mennucci B. Phys. Chem. Chem. Phys. 2013; 15: 6583
- 47 Mennucci B, Cappelli C, Guido CA, Cammi R, Tomasi J. J. Phys. Chem. A 2009; 113: 3009
- 48 Meng S, Caprasecca S, Guido CA, Jurinovich S, Mennucci B. Theor. Chem. Acc. 2015; 134: 150
- 49 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery Jr. JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 16, Revision B. 01. Gaussian Inc.; Wallingford, CT: 2016
- 50 Lyapkalo I, Vogel M, Stark C. Synlett 2007; 2907
- 51 Pangborn AB, Giardello MA, Grubbs RH, Rosen RK, Timmers FJ. Organometallics 1996; 15: 1518
- 52 Cowieson NP, Aragao D, Clift M, Ericsson DJ, Gee C, Harrop SJ, Mudie N, Panjikar S, Price JR, Riboldi-Tunnicliffe A, Williamson R, Caradoc-Davies T. J. Synchrotron Radiat. 2015; 22: 187
- 53 Sheldrick GM. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2015; 71: 3
- 54 Farrugia LJ. J. Appl. Crystallogr. 1997; 30: 565
- 55 Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, Streek J, Wood PA. J. Appl. Crystallogr. 2008; 41: 466
- 56 Brindisi M, Butini S, Franceschini S, Brogi S, Trotta F, Ros S, Cagnotto A, Salmona M, Casagni A, Andreassi M, Saponara S, Gorelli B, Weikop P, Mikkelsen JD, Scheel-Kruger J, Sandager-Nielsen K, Novellino E, Campiani G, Gemma S. J. Med. Chem. 2014; 57: 9578
- 57 Prodanov MF, Diakov MY, Vlasenko GS, Vashchenko VV. Synlett 2015; 26: 1905