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Influence of Self-Assembly and Solvent Polarity on Fluorescence Properties of Hydrophobic Organic Cations Based on Anthracene Skeleton

  • Chunxia TanEmail author
Biology
  • 12 Downloads

Abstract

Fluorescence mode is influenced by the substituents, the polarity of the solvent, the steric factor and even the aggregation state of molecules in solvent under the testing environment. By comparing the fluorescent behavior of three anthracene derivatives, we observe that the hydrophobic interaction and steric effect in structures reduce fluorescence intensity, quantum yield and fluorescence lifetime. The emitting mode of two amphiphilic salts changes from aggregation emission in weak polar solvent to monomer emission in strong polar solvent and gives the similar variety in mixed solvent.

Key words

organic cations fluorescence self-assembly solvent polarity monomer emission aggregation emission 

CLC number

O 651 

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References

  1. [1]
    Fabbrizzi L, Poggi A. Sensors and switches from su-pramolecular chemistry [J]. Chem Soc Rev, 1995, 24: 197–202.CrossRefGoogle Scholar
  2. [2]
    Montalti M, Prodi L, Zaccheroni N. Luminescent chemo-sensors based on anthracene or dioxyxanthone derivatives [J]. Journal of Fluorescence, 2000, 10(2): 71–76.CrossRefGoogle Scholar
  3. [3]
    Cao H, Heagy M D. Fluorescent chemosensors for carbohydrates: A decade’s worth of bright spies for saccharides in review [J]. Journal of Fluorescence, 2004, 14(5): 569–584.CrossRefGoogle Scholar
  4. [4]
    Zhang G, Zhang D, Guo X, et al. A new redox-fluorescence switch based on a triad with tetrathiafulvalene and anthracene units [J]. Org Lett, 2004, 6(8): 1209–1212.CrossRefPubMedGoogle Scholar
  5. [5]
    Zhang D, Su J, Ma X, et al. An efficient multiple-mode molecular logic system for pH, solvent polarity, and Hg2+ ions [J]. Tetrahedron, 2008, 64(36): 8515–8521.CrossRefGoogle Scholar
  6. [6]
    Shiraishi Y, Tokitoh Y, Nishimura G, et al. A molecular switch with pH-controlled absolutely switchable dual-mode fluorescence[J]. Org Lett, 2005, 7(13): 2611–2614.CrossRefPubMedGoogle Scholar
  7. [7]
    Park J, Kim J, Seo M, et al. Dual-mode fluorescence switching induced by self-assembly of well-defined poly(arylene ether sulfone)s containing pyrene and amide moieties [J]. Chem Commun, 2012, 48(85): 10556–10558.CrossRefGoogle Scholar
  8. [8]
    Li G, Magana D, Dyer R B. Direct observation and control of ultrafast photoinduced twisted intramolecular charge transfer (TICT) in triphenyl-methane dyes [J]. J Phys Chem B, 2012, 116(41): 12590–12596.CrossRefPubMedPubMedCentralGoogle Scholar
  9. [9]
    Ryu D, Park E, Kim D S, et al. A rational approach to fluorescence “Turn-On” sensing of α-amino-carboxylates [J]. J Am Chem Soc, 2008, 130(8): 2394–2395.CrossRefPubMedGoogle Scholar
  10. [10]
    Muralidharan S, Sinha H K, Yates K. Conformational effects on charge-transfer properties in selected 9, 10-disubstituted anthracene derivatives: Ground- and excited-state dipole moments [J]. J Phys Chem, 1991, 95(22): 8517–8520.CrossRefGoogle Scholar
  11. [11]
    Aathimanikandan S V, Sandanaraj B S, Arge C G, et al. Effect of guest molecule flexibility in access to dendritic interiors [J]. Org Lett, 2005, 7(14): 2809–2812.CrossRefPubMedGoogle Scholar
  12. [12]
    Kim J, Morozumi T, Kurumatani N, et al. Novel chemosen-sor for alkaline earth metal ion based on 9-anthryl aromatic amide using a naphthalene as a TICT control site and intramolecular energy transfer donor [J]. Tetrahedron Letters, 2008, 49(12): 1984–1987.CrossRefGoogle Scholar
  13. [13]
    Luo J, Xie Z, Lam J W Y, et al. Aggregation induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole [J]. Chem Commun, 2001, (18): 1740–1741.Google Scholar
  14. [14]
    Hong Y, Lam J W Y, Tang B Z. Aggregation-induced emission: Phenomenon, mechanism and applications [J]. Chem Commun, 2009, (29): 4332–4353.Google Scholar
  15. [15]
    Motegi H, Hu L, Slebodnick C, et al. Synthesis and structure of two novel cobalt(II) and zinc(ii) crystalline coordination networks constructed with 1,3,5-benzene tricarboxylate and 9,10-bis(imiidazol-1-ylmethyl)anthracene [J]. Microporous and Mesoporous Materials, 2010, 129(3): 360–365.CrossRefGoogle Scholar
  16. [16]
    Tan C X, Bu W F. Synthesis and energy band characterization of hybrid molecular materials based on organic-polyo-xometalate charge-transfer salts [J]. Journal of Solid State Chemistry, 2014, 219: 93–98.CrossRefGoogle Scholar
  17. [17]
    Azumaya I, Kagechika H, Fujiwara Y, et al. Twisted intramolecular charge-transfer fluorescence of aromatic amides: Conformation of the amide bonds in excited states [J]. J Am Chem Soc, 1991, 113(8): 2833–2838.CrossRefGoogle Scholar
  18. [18]
    Lekha P K, Prasad E. Aggregation-controlled excimer emission from anthracene-containing polyamidoamine den-drimers [J]. Chem Eur J, 2010, 16(12): 3699–3706.CrossRefPubMedGoogle Scholar
  19. [19]
    Zhang H Y, Zhang Z L, Ye K Q, et al. Organic crystals with tunable emission colors based on a single organic molecule and different molecular packing structures [J]. Adv Mater, 2006, 18(18): 2369–2372.CrossRefGoogle Scholar

Copyright information

© Wuhan University and Springer-Verlag GmbH Germany 2019

Authors and Affiliations

  1. 1.College of PharmacyGansu University of Chinese MedicineLanzhou, GansuChina

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