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CC BY-NC-ND 4.0 · Organic Materials 2022; 4(03): 86-101
DOI: 10.1055/a-1910-9165
DOI: 10.1055/a-1910-9165
Supramolecular Chemistry
Original Article
Copper-Templated Formation of Dihelical Oligothiophene–Phenanthroline Assemblies
Abstract
We report the synthesis and comprehensive characterization of a series of (oligo)thiophene-bridged (bis)phenanthroline ligands. The complexation behavior of the ditopic ligands with Cu(I) was explored by high-resolution ESI mass spectrometry, UV-vis spectroscopy, and electrochemistry. Whereas ligands, in which the phenanthrolines are bridged by smaller (oligo)thiophene units, provided mainly mononuclear complexes, quaterthiophene-based ditopic ligands show a strong tendency to undergo metal-templated self-assembly into double-stranded, dinuclear helicates.
Key words
oligothiophenes - phenanthrolines - helicates - copper(I) complexation - optoelectronic propertiesPublication History
Received: 20 June 2022
Accepted after revision: 21 July 2022
Accepted Manuscript online:
27 July 2022
Article published online:
15 September 2022
© 2022. The authors. 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/)
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References
- 1 Fichou D. Handbook of Oligo- and Polythiophenes. Weinheim, Germany: Wiley VCH; 1999
- 2 Roncali J, Leriche P, Cravino A. Adv. Mater. 2007; 19: 2045
- 3 Mishra A, Ma C-Q, Bäuerle P. Chem. Rev. 2009; 109,: 1141
- 4 Mishra A, Bäuerle P. Angew. Chem. Int. Ed. 2012; 51: 2020
- 5 Scharber MC, Mühlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CJ. Adv. Mater. 2006; 18: 789
- 6 Accorsi G, Listorti A, Yoosaf K, Armaroli N. Chem. Soc. Rev. 2009; 38: 1690
- 7 Omoto K, Tashiro S, Kuritani M, Shionoya M. J. Am. Chem. Soc. 2014; 136: 17946
- 8 Ni Z, McDaniel AM, Shores MP. Chem. Sci. 2010; 1: 615
- 9 Holder E, Langeveld BMW, Schubert US. Adv. Mater. 2005; 17: 1109
- 10 Deng Z, Yang X, Yang K, Zhang L, Wang H, Wang X, Sun L. ACS Sustainable Chem. Eng. 2021; 9: 5252
- 11 Saygili Y, Stojanovic M, Flores-Diaz N, Zakeeruddin SM, Vlachopoulos N, Grätzel M, Hagfeldt A. Inorganics 2019; 17: 30
- 12a Kalsani V, Bodenstedt H, Fenske D, Schmittel M. Eur. J. Inorg. Chem. 2005; 2005: 1841
- 12b Kalsani V, Ammon H, Jäckel F, Rabe J, Schmittel M. Chem. Eur. J. 2004; 10: 5481
- 12c Schmittel M. Isr. J. Chem. 2019; 59: 197
- 13a Bäuerle P, Ammann M, Wilde M, Götz G, Mena-Osteritz E, Rang A, Schalley C. Angew. Chem. Int. Ed. 2007; 46: 363
- 13b Ammann M, Bäuerle P. Org. Biomol. Chem. 2005; 3: 4143
- 13c Götz G, Zhu X, Mishra A, Segura J-L, Mena-Osteritz E, Bäuerle P. Chem. Eur. J. 2015; 21: 7193
- 14 Collin J-P, Dietrich-Buchecker CO, Gavina P, Jimenez-Molero MC, Sauvage JP. Acc. Chem. Res. 2001; 34,: 477
- 15 Balzani V, Credi A, Raymo FM, Stoddart JF. Angew. Chem. Int. Ed. 2000; 39: 3348
- 16 Vidal PL, Divisia-Blohorn B, Bidan G, Kern J-M, Sauvage J-P, Hazemann J-L. Inorg. Chem. 1999; 38: 4203
- 17 Kraus T, Budesinky M, Cvacka J, Sauvage J-P. Angew. Chem. Int. Ed. 2006; 45: 258
- 18 Dietrich-Buchecker CO, Rapenne G, Sauvage J-P, De Cian A, Fischer J. Chem. Eur. J. 1999; 5: 1432
- 19 Piguet C, Bernardinelli G, Hopfgartner G. Chem. Rev. 1997; 97: 2005
- 20 Beves JE, Blight BA, Campbell CJ, Leigh DA, McBurney RT. Angew. Chem. Int. Ed. 2011; 123: 9428
- 21 Fielden SDP, Leigh DA, Woltering SL. Angew. Chem. Int. Ed. 2017; 56: 11166
- 22 Velten U, Rehahn M. Chem. Commun. 1996; 2639
- 23 Zong R, Thummel RP. J. Am. Chem. Soc. 2005; 127: 12802
- 24 Zhong R, Wang D, Hammit R, Thummel RP. J. Org. Chem. 2006; 71: 167
- 25 Ruiz-Carretero A, Atoini Y, Han T, Operamolla A, Ippolito S, Valentini C, Carrara S, Sinn S, Prasetyanto EA, Heiser T, Samori P, Farinola G, De Cola L. J. Mater. Chem. A 2019; 7: 16777
- 26 Araki K, Endo H, Masuda G, Ogawa T. Chem. Eur. J. 2004; 10: 3331
- 27 Balzani V, Barigelletti F, De Cola L. Top. Curr. Chem. 1990; 158: 31
- 28 Papenfuss TM, Mann KR. Inorg. Chem. 2001; 40,: 6301
- 29 Cunningham CT, Cunningham KLH, Michalec JF, McMillin DR. Inorg. Chem. 1999; 38: 4388
- 30 Brandl T, Kerzig C, Le Pleux L, Prescimone A, Wenger OS, Mayor M. Chem. Eur. J. 2020; 26: 3119
- 31 Ochs NAK, Lewandowska U, Zajaczkowski W, Corra S, Reger S, Herdlitschka A, Schmid S, Pisula W, Müllen K, Bäuerle P, Wennemers H. Chem. Sci. 2019; 10: 5391
- 32 Stone DA, Hsu L, Stupp SI. Soft Matter 2009; 5: 1990
- 33 Ardonã HAM, Tovar JD. Bioconjugate Chem. 2015; 26: 2290
- 34 Leclere P, Surin M, Viville P, Lazzaroni R, Kilbinger AFM, Henze O, Feast WJ, Cavallini M, Biscarini M, Schenning APH. J, Meijer EW. Chem. Mater. 2004; 16: 4452
- 35 Haid S, Marszalek M, Mishra A, Wielopolski M, Teuscher J, Moser J-E, Humphry-Baker R, Zakeeruddin SM, Grätzel M, Bäuerle P. Adv. Funct. Mater. 2012; 22: 1291
- 36 Linnell RH, Kaczmarczyk A. J. Chem. Phys. 1961; 65: 1196
- 37 Dietrich-Buchecker CO, Sauvage J-P, Kern J-M. J. Am. Chem. Soc. 1989; 111: 7791
- 38 Dietrich-Buchecker CO, Sauvage JP, Armaroli N, Ceroni P, Balzani V. New J. Chem. 1996; 20: 801
- 39 Bäuerle P, Segelbacher U, Maier A, Mehring M. J. Am. Chem. Soc. 1993; 115: 10217
- 40 Sigel J, Balakrishnan RM, Häring UK. J. Am. Chem. Soc. 1985; 107: 5137
- 41 Gütz C, Hovorka R, Struch N, Bunzen J, Eppler GM, Qu ZW, Grimme S, Topic F, Rissanen K, Cetina M, Engeser M, Lützen A. J. Am. Chem. Soc. 2014; 136: 11830
- 42 Przybylski M, Glocker MO. Angew. Chem. Int. Ed. Engl. 1996; 35: 806
- 43a McIndoe JS, Viske KL. J. Mass Spectrom. 2019; 54: 446
- 43b Gross JH. Mass Spectrometry: A Textbook. 3rd ed. Cham: Springer; 2017
- 44 Albrecht M. Chem. Rev. 2001; 101: 3457
- 45 Kern J-M, Sauvage J-P, Weidmann J-L, Armaroli N, Flamigni L, Ceroni P, Balzani V. Inorg. Chem. 1997; 36: 5329
- 46 Vidal P-L, Divisia-Blohorn B, Bidan G, Hazemann J-L, Kern J-M, Sauvage J-P. Chem. Eur. J. 2000; 9,: 1663
- 47 Green O, Gandhi BA, Burstyn JN. Inorg. Chem. 2009; 48: 5704
- 48 Leandri V, Pizzichetti ARP, Xu B, Franchi D, Zhang W, Benesperi I, Freitag M, Sun L, Kloo L, Gardner JM. Inorg. Chem. 2019; 58: 12167
- 49 Armaroli N, Accorsi G, Gisselbrecht JP, Gross M, Eckert J-F, Nierengarten JF. New J. Chem. 2003; 27: 1470
- 50 Dietrich-Buchecker CO, Nierengarten JF, Sauvage JP, Armaroli N, Balzani V, De Cola L. J. Am. Chem. Soc. 1993; 115: 11237
- 51 Ammann M. Ph.D. Thesis. University of Ulm. Germany: 2004