Skip to main content
SpringerLink
Log in

π-Electronic Ion-Pairing Assemblies for Photoswitching Materials

  • Chapter
  • First Online:
Photosynergetic Responses in Molecules and Molecular Aggregates

  • 456 Accesses

Abstract

Ion-pairing assemblies consisting of appropriately designed oppositely charged π-electronic systems give rise to various functional supramolecular assemblies including crystals and soft materials based on the anisotropic orientation of charged species through electrostatic and other weak noncovalent interactions. The introduction of photo-responsive moiety to the charged species facilitated the formation of photo-responsive ion-pairing assemblies, whose assembling modes were controlled by photoirradiation. Furthermore, pyrrole-based π-system–PtII complexes were designed and exhibited unique photo-induced excited-state dynamics.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Faul CFJ, Antonietti M (2003) Ionic self-assembly: facile synthesis of supramolecular materials. Adv Mater 15:673–683

    CAS  Google Scholar 

  2. Faul CFJ (2014) Ionic self-assembly for functional hierachical nanostructured materials. Acc Chem Res 47:3428–3438

    CAS  PubMed  Google Scholar 

  3. Binnemans K (2005) Ionic liquid crystals. Chem Rev 105:4148–4204

    CAS  PubMed  Google Scholar 

  4. Axenov KV, Laschat S (2011) Thermotropic ionic liquid crystals. Materials 4:206–259

    CAS  PubMed  PubMed Central  Google Scholar 

  5. Goossens K, Lava K, Bielawski CW, Binnemans K (2016) Ionic liquid crystals: versatile materials. Chem Rev 116:4643–4807

    CAS  PubMed  Google Scholar 

  6. Haketa Y, Maeda H (2017) Dimension-controlled ion-pairing assemblies based on π-electronic charged species. Chem Commun 53:2894–2909

    CAS  Google Scholar 

  7. Haketa Y, Maeda H (2018) Dimension-controlled π-electronic ion-pairing assemblies. Bull Chem Soc Jpn 91:420–436

    CAS  Google Scholar 

  8. Webster OW (1965) Diazotetracyanocyclopentadiene and its conversion to tetracyanocyclopentadienide and pentacyanocyclopentadienide. J Am Chem Soc 87:1820–1821

    CAS  Google Scholar 

  9. Less RJ, McPartlin M, Rawson JM, Wood PT, Wright DS (2010) A simple approach to coordination compounds of the pentacyanocyclopentadienide anion. Chem Eur J 16:13723–13728

    CAS  PubMed  Google Scholar 

  10. Sakai T, Seo S, Matsuoka J, Mori Y (2013) Synthesis of functionalized tetracyanocyclopentadienides from tetracyanothiophene and sulfones. J Org Chem 78:10978–10985

    CAS  PubMed  Google Scholar 

  11. Bando Y, Haketa Y, Sakurai T, Matsuda W, Seki S, Takaya H, Maeda H (2016) Ion-pairing assemblies based on pentacyano-substituted cyclopentadienide as a π-electronic anion. Chem Eur J 22:7843–7850

    CAS  PubMed  Google Scholar 

  12. Maeda H, Fukui A, Yamakado R, Yasuda N (2015) Dipyrrolyphenol as a precursor of π-electronic anion that forms ion pairs with cations. Chem Commun 51:17572–17575

    CAS  Google Scholar 

  13. Maeda H, Takeda Y, Haketa Y, Morimoto Y, Yasuda N (2018) Ion-pairing assemblies of π-electronic anions formed by intramolecular hydrogen bonding. Chem Eur J 24:8910–8916

    CAS  PubMed  Google Scholar 

  14. Yamakado R, Ishibashi H, Motoyoshi Y, Yasuda N, Maeda H (2019) Ion-pairing assemblies based on π-extended dipyrrolylquinoxalines. Chem Commun 55:326–329

    CAS  Google Scholar 

  15. Sasano Y, Yasuda N, Maeda H (2017) Deprotonated meso-hydroxyporphyrin as a stable π-electronic anion: the building unit of an ion-pairing assembly. Dalton Trans 46:8924–8928

    CAS  PubMed  Google Scholar 

  16. Sasano Y, Haketa Y, Tanaka H, Yasuda N, Hisaki I, Maeda H (2019) Peripheral modifications of meso-hydroxyporphyrins: formation of π-electronic anions and ion-pairing assemblies. Chem Eur J 25:6712–6717

    CAS  PubMed  Google Scholar 

  17. Haketa Y, Bando Y, Sasano Y, Tanaka H, Yasuda N, Hisaki I, Maeda H (2019) Liquid crystals comprising π-electronic ions from porphyrin–AuIII complexes. iScience 14:241–256

    Google Scholar 

  18. Tanaka H, Haketa Y, Yasuda N, Maeda H (2019) Substitution-pattern- and counteranion-depending ion-pairing assemblies based on electron-deficient porphyrin–AuIII complexes. Chem Asian J 14:2129–2137

    CAS  PubMed  Google Scholar 

  19. Maeda H, Bando Y (2013) Recent progress in research on anion-responsive pyrrole-based π-conjugated acyclic molecules. Chem Commun 49:4100–4113

    CAS  Google Scholar 

  20. Haketa Y, Maeda H (2011) From helix to macrocycle: anion-driven conformation control of π-conjugated acyclic oligopyrroles. Chem Eur J 17:1485–1492

    CAS  PubMed  Google Scholar 

  21. Haketa Y, Bando Y, Takaishi K, Uchiyama M, Muranaka A, Naito M, Shibaguchi H, Kawai T, Maeda H (2012) Asymmetric induction in the preparation of helical receptor-anion complexes: ion-pair formation with chiral cations. Angew Chem Int Ed 51:7967–7971

    CAS  Google Scholar 

  22. Sasano Y, Yasuda N, Maeda H (2016) Negatively charged π-electronic systems by deprotonation of hydroxy-substituted dipyrrolyldiketone boron complexes. Chem Asian J 11:3423–3429

    CAS  PubMed  Google Scholar 

  23. Maeda H, Ito Y (2006) BF2 complex of fluorinated dipyrrolyldiketone: a new class of efficient receptor for acetate anions. Inorg Chem 45:8205–8210

    CAS  PubMed  Google Scholar 

  24. Maeda H, Kinoshita K, Naritani K, Bando Y (2011) Self-sorting self-complementary assemblies of π-conjugated acyclic anion receptors. Chem Commun 47:8241–8243

    CAS  Google Scholar 

  25. Maeda H, Naritani K, Honsho Y, Seki S (2011) Anion modules: building blocks of supramolecular assemblies by combination with π-conjugated anion receptors. J Am Chem Soc 133:8896–8899

    CAS  PubMed  Google Scholar 

  26. Maeda H, Okubo T, Haketa Y, Yasuda N (2018) Pyrrole-based zwitterionic π-electronic systems that form self-assembled dimers. Chem Eur J 24:16176–16182

    CAS  PubMed  Google Scholar 

  27. Sekiya R, Tsutsui Y, Choi W, Sakurai T, Seki S, Bando Y, Maeda H (2014) Ion-based assemblies of planar anion complexes and cationic PtII complexes. Chem Commun 50:10615–10618

    CAS  Google Scholar 

  28. Dong B, Sakurai T, Bando Y, Seki S, Takaishi K, Uchiyama M, Muranaka A, Maeda H (2013) Ion-based materials derived from positively and negatively charged chloride complexes of π-conjugated molecules. J Am Chem Soc 135:14797–14805

    CAS  PubMed  Google Scholar 

  29. Dong B, Sakurai T, Honsho Y, Seki S, Maeda H (2013) Cation modules as building blocks forming supramolecular assemblies with planar receptor-anion complexes. J Am Chem Soc 135:1284–1287

    CAS  PubMed  Google Scholar 

  30. Xu JF, Chen YZ, Wu D, Wu LZ, Tung CH, Yang QZ (2013) Photoresponsive hydrogen-bonded supramolecular polymers based on a stiff stilbene unit. Angew Chem Int Ed 52:9738–9742

    CAS  Google Scholar 

  31. Xia D, Yu G, Li J, Huang F (2014) Photo-responsive self-assembly based on a water-soluble pillar[6]arene and an azobenzene-containing amphiphile in water. Chem Commun 50:3606–3608

    CAS  Google Scholar 

  32. Yokoyama S, Hirose T, Matsuda K (2014) Phototriggered formation and disappearance of surface-confined self-assembly composed of photochromic 2-thienyl-type diarylethene: a cooperative model at the liquid/solid interface. Chem Commun 50:5964–5966

    CAS  Google Scholar 

  33. Bandara HMD, Burdette SC (2012) Photoisomerization in different classes of azobenzene. Chem Soc Rev 41:1809–1825

    CAS  PubMed  Google Scholar 

  34. Ichimura K (2000) Photoalignment of liquid-crystal systems. Chem Rev 100:1847–1873

    CAS  PubMed  Google Scholar 

  35. Yu H, Ikeda T (2011) Photocontrollable liquid-crystalline actuators. Adv Mater 23:2149–2180

    CAS  PubMed  Google Scholar 

  36. Bisoyi HK, Li Q (2016) Light-driven liquid crystalline materials: from photo-induced phase transitions and property modulations to applications. Chem Rev 116:15089–15166

    CAS  PubMed  Google Scholar 

  37. Ichimura K (2009) Reversible photoisomerisability and particle size changes of mill-dispersed azobenzene crystals in water. Chem Commun 1496–1498

    Google Scholar 

  38. Yamakado R, Hara M, Nagano S, Seki T, Maeda H (2017) Photo-responsive soft ionic crystals: ion-pairing assemblies of azobenzene carboxylates. Chem Eur J 23:9244–9248

    CAS  PubMed  Google Scholar 

  39. Maeda H, Terasaki M, Haketa Y, Mihashi Y, Kusunose Y (2008) BF2 complexes of α-alkyl-substituted dipyrrolyldiketones as acyclic anion receptors. Org Biomol Chem 6:433–436

    CAS  PubMed  Google Scholar 

  40. Yamakado R, Hara M, Nagano S, Seki T, Maeda H (2018) Complexation of anion-responsive π-electronic system with alkyl-substituted azobenzene carboxylate providing ion-pairing assemblies. Chem Lett 47:404–407

    CAS  Google Scholar 

  41. Hoshino M, Uchida E, Norikane Y, Azumi R, Nozawa S, Tomita A, Sato T, Adachi S, Koshihara S (2014) Crystal melting by light: X-ray crystal structure analysis of an azo crystal showing photoinduced crystal-melt transition. J Am Chem Soc 136:9158–9164

    CAS  PubMed  Google Scholar 

  42. Yamakado R, Haketa Y, Hara M, Nagano S, Seki T, Maeda H (2019) Photo-responsive dimension-controlled ion-pairing assemblies based on anion complexes of π-electronic systems. Chem Commun 55:10269–10272

    CAS  Google Scholar 

  43. Williams JAG, Develay S, Rochester DL, Murphy L (2008) Optimising the luminescence of platinum(II) complexes and their application in organic light emitting devices (OLEDs). Coord Chem Rev 252:2596–2611

    Google Scholar 

  44. Hirata G, Kobayashi Y, Sato R, Shigeta Y, Yasuda N, Maeda H (2019) Pyrrole-based π-system–PtII complexes: chiroptical properties and excited-state dynamics with microsecond triplet lifetimes. Chem Eur J 25:8797–8804

    CAS  PubMed  Google Scholar 

  45. Penfold TJ, Gindensperger E, Daniel C, Marian CM (2018) Spin-vibronic mechanism for intersystem crossing. Chem Rev 118:6975–7025

    CAS  PubMed  Google Scholar 

  46. Nakagawa T, Okamoto K, Hanada H, Katoh R (2016) Probing with randomly interleaved pulse train bridges the gap between ultrafast pump-probe and nanosecond flash photolysis. Opt Lett 41:1498–1501

    PubMed  Google Scholar 

  47. Kita H, Yamakado R, Fukuuchi R, Konishi T, Kamada K, Haketa Y, Maeda H (2020) Switching of two-photon optical properties by anion binding of pyrrole-based boron diketonates through conformation change. Chem Eur J 26:3404–3410

    Google Scholar 

  48. Tanaka H, Haketa Y, Bando Y, Yamakado R, Yasuda N, Maeda H (2020) Ion-pairing assemblies of porphyrin–AuIII complexes in combination with π-electronic receptor–anion complexes. Chem Asian J 15:494–498

    Google Scholar 

Download references

Acknowledgements

We deeply appreciate the co-authors of the reports related with the contents in this chapter, including Dr. Mitsuo Hara (Nagoya University), Prof. Shusaku Nagano (Rikkyo University), Prof. Takahiro Seki (Nagoya University), Dr. Ryoma Sato (RIKEN), Prof. Yasuteru Shigeta (the University of Tsukuba), Prof. Yoichi Kobayashi (Ritsumeikan University), and Dr. Nobuhiro Yasuda (JASRI), for their collaboration. The present work was supported by JSPS KAKENHI Grant Number 26107007, Grant-in-Aid for Scientific Research on Innovative Areas “Photosynergetics”.

Author information

Authors and Affiliations

  1. Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu, Shiga, 525–8577, Japan

    Yohei Haketa, Kazuki Urakawa & Hiromitsu Maeda

  2. Department of Organic Materials Science, Graduate School of Organic Materials Science, Yamagata University, Yonezawa, Yamagata, 992–8510, Japan

    Ryohei Yamakado

Authors
  1. Yohei Haketa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ryohei Yamakado
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kazuki Urakawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hiromitsu Maeda
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hiromitsu Maeda .

Editor information

Editors and Affiliations

  1. Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, Japan

    Hiroshi Miyasaka

  2. Graduate School of Engineering, Kyoto University, Kyoto, Japan

    Kenji Matsuda

  3. Department of Chemistry, Aoyama Gakuin University, Sagamihara, Kanagawa, Japan

    Jiro Abe

  4. Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara, Japan

    Tsuyoshi Kawai

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer Nature Singapore Pte Ltd.

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Haketa, Y., Yamakado, R., Urakawa, K., Maeda, H. (2020). π-Electronic Ion-Pairing Assemblies for Photoswitching Materials. In: Miyasaka, H., Matsuda, K., Abe, J., Kawai, T. (eds) Photosynergetic Responses in Molecules and Molecular Aggregates. Springer, Singapore. https://doi.org/10.1007/978-981-15-5451-3_18

Download citation

Publish with us

Policies and ethics

Search

Navigation