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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(01): 047-063
DOI: 10.1055/s-0040-1708502
Focus Issue: Structure to Function in Supramolecular Polymers and Materials
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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/). (2020) The Author(s).

Recent Progress in Hydrogen-Bonded π-Conjugated Systems Displaying J-Type Aggregates

Nelson Ricardo Ávila-Rovelo 
a   Institute Charles Sadron, CNRS, University of Strasbourg, 23 Rue du Loess, BP 84047, 67034 Strasbourg, Cedex 2, France
,
Amparo Ruiz-Carretero
a   Institute Charles Sadron, CNRS, University of Strasbourg, 23 Rue du Loess, BP 84047, 67034 Strasbourg, Cedex 2, France
› Author Affiliations Funding Information LabEx Emerging Investigators Grant 2018 from the Fondation pour la Recherche en Chimie.
Further Information

Publication History

Received: 26 December 2019

Accepted after revision: 10 February 2020

Publication Date:
30 March 2020 (online)

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Abstract

Supramolecular approaches are of great interest in the design of functional materials. The types of aggregates arising from different noncovalent interactions endow materials with intriguing properties. In this sense, J-type aggregates are very attractive due to their unique optical properties and capacity to transport excitons. These features make them great candidates in the design of materials for organic electronic devices. Furthermore, the incorporation of additional hydrogen-bonding functionalities provides J-aggregates with superior directionality and connection among the different π-conjugated cores. The control over the formation of H-bonds to achieve functional aggregates is therefore a promising strategy towards controlled structures with specific functions.

This review outlines the most relevant and recent works of π-conjugated systems exhibiting J-type aggregates resulting from hydrogen-bonding interactions. Different types of hydrogen-bonding functionalities will be discussed together with their roles in the aggregate properties, their impact in the optoelectronic properties, the self-assembly mechanisms, and their applications in organic electronics.

Key words

Hydrogen-bonding - J-aggregates - organic electronics
 

  • References

  • 1 Lehn J-M. Angew. Chem. Int. Ed. 1988; 27: 89
    CrossrefPubMed
  • 2 Lehn J-M. Eur. Rev. 2009; 17: 263
    CrossrefPubMed
  • 3 Lehn J-M. Angew. Chem. Int. Ed. 1990; 29: 1304
    CrossrefPubMed
  • 4 Fyfe MC. T, Stoddart JF. Acc. Chem. Res. 1997; 30: 393
    CrossrefPubMed
  • 5 Stupp SI, Palmer LC. Chem. Mater. 2014; 26: 507
    CrossrefPubMed
  • 6 Wong K-T, Bassani DM. NPG Asia Mater. 2014; 6: e116
    CrossrefPubMed
  • 7 González-Rodríguez D, Schenning AP. H. J. Chem. Mater. 2011; 23: 310
    CrossrefPubMed
  • 8 Steiner T. Angew. Chem. Int. Ed. 2002; 41: 49
    PubMed
  • 9 Prins LJ, Reinhoudt DN, Timmerman P. Angew. Chem. Int. Ed. 2001; 40: 2382
    CrossrefPubMed
  • 10 Gospodinova N, Tomšík E. Prog. Polym. Sci. 2015; 43: 33
    CrossrefPubMed
  • 11 Schenning AP. H. J, , V Herrikhuyzen J, Jonkheijm P, Chen Z, Würthner F, Meijer EW. J. Am. Chem. Soc. 2002; 124: 10252
    CrossrefPubMed
  • 12 Schoonbeek FS, van Esch JH, Wegewijs B, Rep DB. A, Haas Md. e, Klapwijk TM, Kellogg RM, Feringa BL. Angew. Chem. Int. Ed. 1999; 38: 1393
    CrossrefPubMed
  • 13 Würthner F, Thalacker C, Sautter A. Adv. Mater. 1999; 11: 754
    CrossrefPubMed
  • 14 Bohanon TM, Denzinger S, Fink R, Paulus W, Ringsdorf H, Weck M. Angew. Chem. Int. Ed. 1995; 34: 58
    CrossrefPubMed
  • 15 Jelley EE. Nature 1937; 139: 631
    CrossrefPubMed
  • 16 Scheibe G. Angew. Chem. 1937; 50: 212
    CrossrefPubMed
  • 17 Bücher H, Kuhn H. Chem. Phys. Lett. 1970; 6: 183
    CrossrefPubMed
  • 18 Knoester J, Agranovich VM. Frenkel and charge-transfer excitons in organic solids. In: Thin Films and Nanostructures. Academic Press. Amsterdam: 2003: 1-96 (Internet: http://www.sciencedirect.com/science/article/pii/S1079405003310014 )
    PubMedGoogle Scholar
  • 19 Hestand NJ, Spano FC. Chem. Rev. 2018; 118: 7069
    CrossrefPubMed
  • 20 Shirakawa M, Kawano S, Fujita N, Sada K, Shinkai S. J. Org. Chem. 2003; 68: 5037
    CrossrefPubMed
  • 21 Tani T. Imaging Sci. J. 2007; 55: 65
    CrossrefPubMed
  • 22 Kawaguchi T, Iwata K. Thin Solid Films 1990; 191: 173
    CrossrefPubMed
  • 23 Paternò GM, Moretti L, Barker AJ, D'Andrea C, Luzio A, Barbero N, Galliano S, Barolo C, Lanzani G, Scotognella F. J. Mater. Chem. C 2017; 5: 7732
    CrossrefPubMed
  • 24 Kaiser TE, Stepanenko V, Würthner F. J. Am. Chem. Soc. 2009; 131: 6719
    CrossrefPubMed
  • 25 Würthner F, Thalacker C, Diele S, Tschierske C. Chem. Eur. J. 2001; 7: 2245
    CrossrefPubMed
  • 26 Crusats J, El-Hachemi Z, Escudero C, Ribó JM. J. Porphyrins Phthalocyanines 2009; 13: 461
    CrossrefPubMed
  • 27 Song Q, Jiao Y, Wang Z, Zhang X. Small 2016; 12: 24
    CrossrefPubMed
  • 28 Zhou Y, Guzman CX, Helguero-Kelley LC, Liu C, Peurifoy SR, Captain B, Braunschweig AB. J. Phys. Org. Chem. 2016; 29: 689
    CrossrefPubMed
  • 29 Ruiz-Carretero A, Rovelo NRÁ, Militzer S, Mésini PJ. J. Mater. Chem. A 2019; 7: 23451
    CrossrefPubMed
  • 30 Löhner A, Kunsel T, Röhr MI. S, Jansen TL. C, Sengupta S, Würthner F, Knoester J, Köhler J. J. Phys. Chem. Lett. 2019; 10: 2715
    CrossrefPubMed
  • 31 Brixner T, Hildner R, Köhler J, Lambert C, Würthner F. Adv. Energy Mater. 2017; 7: 1700236
    CrossrefPubMed
  • 32 Egawa Y, Hayashida R, Anzai J. Langmuir 2007; 23: 13146
    CrossrefPubMed
  • 33 Fidder H, Terpstra J, Wiersma DA. J. Chem. Phys. 1991; 94: 6895
    CrossrefPubMed
  • 34 Ghosh PN. Solid State Commun. 1976; 19: 639
    CrossrefPubMed
  • 35 Scheblykin IG, Bataiev MM, Van der Auweraer M, Vitukhnovsky AG. Chem. Phys. Lett. 2000; 316: 37
    CrossrefPubMed
  • 36 Scheblykin IG, Sliusarenko OY, Lepnev LS, Vitukhnovsky AG, Van der Auweraer M. J. Phys. Chem. B 2001; 105: 4636
    CrossrefPubMed
  • 37 Dahlbom M, Pullerits T, Mukamel S, Sundström V. J. Phys. Chem. B 2001; 105: 5515
    CrossrefPubMed
  • 38 Kühn O, Sundström V, Pullerits T. Chem. Phys. 2002; 275: 15
    CrossrefPubMed
  • 39 Lin H, Camacho R, Tian Y, Kaiser TE, Würthner F, Scheblykin IG. Nano Lett. 2010; 10: 620
    CrossrefPubMed
  • 40 Würthner F, Kaiser TE, Saha-Möller CR. Angew. Chem. Int. Ed. 2011; 50: 3376
    CrossrefPubMed
  • 41 Spano FC. Acc. Chem. Res. 2010; 43: 429
    CrossrefPubMed
  • 42 Más-Montoya M, Janssen RA. J. Adv. Funct. Mater. 2017; 27: 1605779
    CrossrefPubMed
  • 43 Zhong C, Bialas D, Spano FC. J. Phys. Chem. C 2020; 124: 2146
    CrossrefPubMed
  • 44 Johansson A, Kollman P, Rothenberg S, McKelvey J. J. Am. Chem. Soc. 1974; 96: 3794
    CrossrefPubMed
  • 45 Tsai W-W, Tevis ID, Tayi AS, Cui H, Stupp SI. J. Phys. Chem. B 2010; 114: 14778
    CrossrefPubMed
  • 46 Tevis ID, Tsai W-W, Palmer LC, Aytun T, Stupp SI. ACS Nano 2012; 6: 2032
    CrossrefPubMed
  • 47 Ghosh S, Cherumukkil S, Suresh CH, Ajayaghosh A. Adv. Mater. 2017; 29: 1703783
    CrossrefPubMed
  • 48 Ghosh S, Das S, Saeki A, Praveen VK, Seki S, Ajayaghosh A. ChemNanoMat 2018; 4: 831
    CrossrefPubMed
  • 49 Kaneko R, Chowdhury TH, Sugawa K, Lee J-J, Otsuki J, Islam A. Sol. Energy 2019; 194: 248
    CrossrefPubMed
  • 50 Würthner F. Chem. Commun. 2004; 14: 1564
    CrossrefPubMed
  • 51 Ghosh S, Li X-Q, Stepanenko V, Würthner F. Chem. Eur. J. 2008; 14: 11343
    CrossrefPubMed
  • 52 Wagner W, Wehner M, Stepanenko V, Ogi S, Würthner F. Angew. Chem. Int. Ed. 2017; 56: 16008
    CrossrefPubMed
  • 53 Ogi S, Stepanenko V, Sugiyasu K, Takeuchi M, Würthner F. J. Am. Chem. Soc. 2015; 137: 3300
    CrossrefPubMed
  • 54 Ogi S, Stepanenko V, Thein J, Würthner F. J. Am. Chem. Soc. 2016; 138: 670
    CrossrefPubMed
  • 55 Marciniak H, Li X-Q, Würthner F, Lochbrunner S. J. Phys. Chem. A 2011; 115: 648
    CrossrefPubMed
  • 56 Wolter S, Aizezers J, Fennel F, Seidel M, Würthner F, Kühn O, Lochbrunner S. New J. Phys. 2012; 14: 105027
    CrossrefPubMed
  • 57 Wolter S, Westphal KM, Hempel M, Würthner F, Kühn O, Lochbrunner S. J. Phys. B: At. Mol. Opt. Phys. 2017; 50: 184005
    CrossrefPubMed
  • 58 Fennel F, Wolter S, Xie Z, Plötz P-A, Kühn O, Würthner F, Lochbrunner S. J. Am. Chem. Soc. 2013; 135: 18722
    CrossrefPubMed
  • 59 Ogi S, Fukaya N, , Arifin, Skjelstad BB, Hijikata Y, Yamaguchi S. Chem. Eur. J. 2019; 25: 7303
    CrossrefPubMed
  • 60 Zou Q, Liu K, Abbas M, Yan X. Adv. Mater. 2016; 28: 1031
    CrossrefPubMed
  • 61 Smith KH, Tejeda-Montes E, Poch M, Mata A. Chem Soc Rev 2011; 40: 4563
    CrossrefPubMed
  • 62 Sun Y, Jiang L, Schuermann KC, Adriaens W, Zhang L, Boey FY. C, De Cola L, Brunsveld L, Chen X. Chem. Eur. J. 2011; 17: 4746
    CrossrefPubMed
  • 63 Kumar RJ, MacDonald JM, Singh TB, Waddington LJ, Holmes AB. J. Am. Chem. Soc. 2011; 133: 8564
    CrossrefPubMed
  • 64 Jintoku H, Sagawa T, Miyamoto K, Takafuji M, Ihara H. Chem. Commun. 2010; 46: 7208
    CrossrefPubMed
  • 65 Koti AS. R, Periasamy N. Chem. Mater. 2003; 15: 369
    CrossrefPubMed
  • 66 Kim JH, Lee M, Lee JS, Park CB. Angew. Chem. Int. Ed. 2012; 51: 517
    CrossrefPubMed
  • 67 Xue B, Li Y, Yang F, Zhang C, Qin M, Cao Y, Wang W. Nanoscale 2014; 6: 7832
    CrossrefPubMed
  • 68 Kim JH, Nam DH, Lee YW, Nam YS, Park CB. Small 2014; 10: 1272
    CrossrefPubMed
  • 69 Smith AM, Williams RJ, Tang C, Coppo P, Collins RF, Turner ML, Saiani A, Ulijn RV. Adv. Mater. 2008; 20: 37
    CrossrefPubMed
  • 70 Shimizu LS, Smith MD, Hughes AD, Shimizu KD. Chem. Commun. 2001; 1592
    CrossrefPubMed
  • 71 Shimizu LS, Salpage SR, Korous AA. Acc. Chem. Res. 2014; 47: 2116
    CrossrefPubMed
  • 72 Simic V, Bouteiller L, Jalabert M. J. Am. Chem. Soc. 2003; 125: 13148
    CrossrefPubMed
  • 73 Isare B, Pensec S, Raynal M, Bouteiller L. C. R. Chim. 2016; 19: 148
    CrossrefPubMed
  • 74 Das A, Ghosh S. Chem. Eur. J. 2010; 16: 13622
    CrossrefPubMed
  • 75 Liu Y, Liu L, Zhu E, Yue M, Gao C, Wu X, Che G, Liu H. ChemPlusChem 2018; 83: 1109
    CrossrefPubMed
  • 76 Shoji S, Ogawa T, Hashishin T, Tamiaki H. ChemPhysChem 2018; 19: 913
    CrossrefPubMed
  • 77 Shoji S, Ogawa T, Matsubara S, Tamiaki H. Sci. Rep. 2019; 9: 14006
    CrossrefPubMed
  • 78 Kar H, Gehrig DW, Allampally NK, Fernández G, Laquai F, Ghosh S. Chem. Sci. 2016; 7: 1115
    CrossrefPubMed
  • 79 Yagai S, Kitamoto Y, Datta S, Adhikari B. Acc. Chem. Res. 2019; 52: 1325
    CrossrefPubMed
  • 80 Yagai S, Goto Y, Lin X, Karatsu T, Kitamura A, Kuzuhara D, Yamada H, Kikkawa Y, Saeki A, Seki S. Angew. Chem. Int. Ed. 2012; 51: 6643
    CrossrefPubMed
  • 81 Adhikari B, Yamada Y, Yamauchi M, Wakita K, Lin X, Aratsu K, Ohba T, Karatsu T, Hollamby MJ, Shimizu N, Takagi H, Haruki R, Adachi S, Yagai S. Nat. Commun. 2017; 8: 15254
    CrossrefPubMed
  • 82 Iwaura R, Ohnishi-Kameyama M, Iizawa T. Chem. Eur. J. 2009; 15: 3729
    CrossrefPubMed
  • 83 Mandal S, Zhou X, Lin S, Yan H, Woodbury N. Bioconjugate Chem. 2019; 30: 1870
    CrossrefPubMed
  • 84 Banal JL, Kondo T, Veneziano R, Bathe M, Schlau-Cohen GS. J. Phys. Chem. Lett. 2017; 8: 5827
    CrossrefPubMed
  • 85 Boulais É, Sawaya NP. D, Veneziano R, Andreoni A, Banal JL, Kondo T, Mandal S, Lin S, Schlau-Cohen GS, Woodbury NW, Yan H, Aspuru-Guzik A, Bathe M. Nat. Mater. 2018; 17: 159
    CrossrefPubMed
  • 86 Markova LI, Malinovskii VL, Patsenker LD, Häner Rv. s. Chem. Commun. 2013; 49: 5298
    CrossrefPubMed
  • 87 Zhou Y, Guzman CX, Helguero-Kelley LC, Liu C, Peurifoy SR, Captain B, Braunschweig AB. J. Phys. Org. Chem. 2016; 29: 689
    CrossrefPubMed
  • 88 Levine AM, Schierl C, Basel BS, Ahmed M, Camargo BA, Guldi DM, Braunschweig AB. J. Phys. Chem. C 2019; 123: 1587
    CrossrefPubMed
  • 89 Villari V, Mineo P, Scamporrino E, Micali N. RSC Adv. 2012; 2: 12989
    CrossrefPubMed
  • 90 Militzer S, Tran TM. P, Mésini PJ, Ruiz-Carretero A. ChemNanoMat 2018; 4: 790
    CrossrefPubMed
  • 91 Herbst S, Soberats B, Leowanawat P, Lehmann M, Würthner F. Angew. Chem. Int. Ed. 2017; 56: 2162
    CrossrefPubMed
  • 92 Herbst S, Soberats B, Leowanawat P, Stolte M, Lehmann M, Würthner F. Nat. Commun. 2018; 9: 2646
    CrossrefPubMed
  • 93 Hecht M, Schlossarek T, Stolte M, Lehmann M, Würthner F. Angew. Chem. Int. Ed. 2019; 58: 12979
    CrossrefPubMed