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Chiral assembly of achiral pseudoisocyanine with D- and L-phenylalanine

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Abstract

Supramolecular chirality and molecular self-assembly are important and interesting phenomena in living and non-living systems. In this work, supramolecular chirality of achiral pseudoisocyanine (PIC) J-aggregates was successfully induced by D-, L-phenylalanine (Phe) and other amino acids in NaCl solution. The chiral J-aggregates showed a characteristic, induced circular dichroism (ICD) in the visible region of J-band chromophore which depends on the absolute configuration, concentration and side groups of α-amino acids, as well as temperature. The atomic force microscopy images indicated that the J-aggregates exist in large bundles of entangled nanofibers, and the observed ICD might result from the macroscopic helical arrangement of the assemblies.

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References

  1. Yashima E, Maeda k, Okamoto Y. Memory of macromolecular helicity assisted by interaction with achiral small molecules. Nature, 1999, 399(6735): 449–451

    Article  CAS  Google Scholar 

  2. Van Bommel K J C, Friggeri A, Shinkai S. Organic templates for the generation of inorganic materials. Angew Chem Int Ed, 2003, 42(9): 980–999

    Article  Google Scholar 

  3. Keizer H M, Sijbesma R P. Hierarchical self-assembly of columnar aggregates. Chem Soc Rev, 2005, 34(3): 226–234

    Article  CAS  Google Scholar 

  4. Maeda K, Yashima E. Dynamic helical structures: detection and amplification of chirality. Top Curr Chem, 2006, 265: 47–88

    Article  CAS  Google Scholar 

  5. Hannah K C, Armitage B A. DNA-templated assembly of helical cyanine dye aggregates: A supramolecular chain polymerization. Acc Chem Res, 2004, 37(11): 845–853

    Article  CAS  Google Scholar 

  6. Morikawa M, Yoshihara M, Endo T, Kimizuka N. ATP as building blocks for the self-assembly of excitonic nanowires. J Am Chem Soc, 2005, 127(5): 1358–1359

    Article  CAS  Google Scholar 

  7. Kim O-K, Je J, Jernigan G, Buckley L, Whitten D. Super-helix formation induced by cyanine J-aggregates onto random-coil carboxymethyl amylose as template. J Am Chem Soc, 2006, 128(2): 510–516

    Article  CAS  Google Scholar 

  8. Zhang Y, Xiang J, Tang Y, Xu G, Yan W. Chiral transformation of achiral J-aggregates of a cyanine dye templated by human serum albumin. ChemPhysChem, 2007, 8(2): 224–226

    Article  CAS  Google Scholar 

  9. Pasternack R F, Giannetto A. Self-assembly of porphyrins on nucleic acids and polypeptides. J Am Chem Soc, 1991, 113(20): 7799–7800

    Article  CAS  Google Scholar 

  10. Lauceri R, Raudino A, Scolaro L M, Micali N, Purrello R. From achiral porphyrins to template-imprinted chiral aggregates and further: Self-replication of chiral memory from scratch. J Am Chem Soc, 2002, 124(6): 894–895

    Article  CAS  Google Scholar 

  11. Chen P, Ma X, Liu M. Chirality amplification of porphyrin assemblies exclusively constructed from achiral porphyrin derivatives. ChemPhysChem, 2006, 7(11): 2419–2423

    Article  CAS  Google Scholar 

  12. Onouchi H, Miyagawa T, Morino K, Yashima E. Assisted formation of chiral porphyrin homoaggregates by an induced helical poly-(phenylacetylene) template and their chiral memory. Angew Chem Int Ed, 2006, 45(20): 2381–2384

    Article  CAS  Google Scholar 

  13. De Rossi U, Dahne S, Meskers S C J, Dekkers H. P J M. Spontaneous formation of chirality in J-aggregates showing Davydov splittling. Angew Chem Int Ed, 1996, 35(7): 760–763

    Article  Google Scholar 

  14. Ribo J M, Crusats J, Sagues F, Claret J, Rubires R. Chiral sign induction by vortices during the formation of mesophases in stirred solutions. Science, 2001, 292(5524): 2063–2066

    Article  CAS  Google Scholar 

  15. Jelley E E. Spectral absorption and fluorescence of dyes in the molecular state. Nature, 1936, 138: 1009–1010

    Article  CAS  Google Scholar 

  16. Higgins D, Barbara P. Excitonic transitions in J-aggregates probed by near-field scanning optical microscopy. J Phys Chem, 1995, 99(1): 3–7

    Article  CAS  Google Scholar 

  17. Berlepsch H V, Bottcher C, Dahne L. Structure of J-aggregates of pseudoisocyanine dye in aqueous solution. J Phys Chem B, 2000, 104(37): 8792–8799

    Article  CAS  Google Scholar 

  18. Berlepsch H V, Bottcher C. Network superstructure of pseudoisocyanine J-aggregates in aqueous sodium chloride solution revealed by cryo-transmission electron microscopy. J Phys Chem B, 2002, 106(12): 3146

    Article  CAS  Google Scholar 

  19. Yao H, Sugiyama S, Kawabata R, Ikeda H, Matsuoka O, Yamamoto S, Kitamura N. Spectroscopic and AFM studies on the structures of pseudoisocyanine J-aggregates at a mica/water interface. J Phys Chem B, 1999, 103(21): 4452–4456

    Article  CAS  Google Scholar 

  20. Struganova I. Dynamics of formation of 1,1′-Diethyl-2,2′-cyanine iodide J-aggregates in solution. J Phys Chem A, 2000, 104(43): 9670–9674

    Article  CAS  Google Scholar 

  21. Struganova I A, Hazell M, Gaitor J, McNally-Carr D, Zivanovic S. Influence of inorganic salts and bases on the J-band in the absorption spectra of water solutions of 1,1′-diethyl-2,2′-cyanine iodide. J Phys Chem A, 2003, 107(15): 2650–2656

    Article  CAS  Google Scholar 

  22. Renge I, Wild U P. Solvent, temperature, and excitonic effects in the optical spectra of pseudoisocyanine monomer and J-aggregates. J Phys Chem A, 1997, 101(43): 7977–7988

    Article  CAS  Google Scholar 

  23. Stryer L, Blout E R. Optical Rotatory Dispersion of dyes bound to macromolecules. Cationic dyes: polyglutamic acid complexes. J Am Chem Soc, 1961, 83(6): 1411–1418

    Article  CAS  Google Scholar 

  24. Mason S F. Helical polymerisation of pseudoisocyanine. Proc Chem Soc, 1964, 119

  25. Ringler P, Schulz G E. Self-assembly of proteins into designed networks. Science, 2003, 302(5642): 106–109

    Article  CAS  Google Scholar 

  26. Slavnova T D, Gorner H, Chibisov A K. J-aggregation of anionic ethyl meso-thiacarbocyanine dyes induced by binding to proteins. J Phys Chem B, 2007, 111(33): 10023–10031

    Article  CAS  Google Scholar 

  27. Wang M, Silva G L, Armitage B A. DNA-templated formation of a helical cyanine dye J-aggregate. J Am Chem Soc, 2000, 122(41): 9977–9986

    Article  CAS  Google Scholar 

  28. Garoff R A, Litzinger E A, Connor R E, Fishman I B, Armitage A. Helical aggregation of cyanine dyes on DNA templates: effect of dye structure on formation of homo- and heteroaggregates. Langmuir, 2002, 18(16): 6330–6337

    Article  CAS  Google Scholar 

  29. Shiraki T, Morikawa M, Kimizuka N. Amplification of molecular information through self-assembly: Nanofibers formed from amino acids and cyanine dyes by extended molecular pairing. Angew Chem Int Ed, 2008, 47(1): 106–108

    Article  CAS  Google Scholar 

  30. Spitz C, Dahne S, Ouart A, Abraham H W. Proof of chirality of J-aggregates spontaneously and enantioselectively generated from achiral Dyes. J Phys Chem B, 2000, 104(36): 8664–8669

    Article  CAS  Google Scholar 

  31. Norden B. Linear and circular dichroism of polymeric pseudoisocyanine. J Phys Chem, 1977, 81(2): 151–159

    Article  CAS  Google Scholar 

  32. Daltrazzo E, Scheibe G, Gschwind K, Haimerl F. On the structure of the J-aggregates of pseudoisocyanine. Photogr Sci Eng, 1974, 18(4): 441–450

    Google Scholar 

  33. Gagel R, Gadonas R, Laubereau A. Evidence for biexcitons and dynamic Stark effect in J-aggregates from femtosecond spectroscopy. Chem Phys Lett, 1994, 217(3): 228–233

    Article  CAS  Google Scholar 

  34. Khairutdinov R F, Serpone N, Photophysics of cyanine dyes: Subnanosecond relaxation dynamics in monomers, dimers, and H- and J-aggregates in solution. J Phys Chem B, 1997, 101(14): 2602–2610

    Article  CAS  Google Scholar 

  35. Van Gestel J, Palmans A R A, Titulaer B, Vekemans J A J M, Meijer E W J. “Majority-rules” operative in chiral columnar stacks of C3- symmetrical molecules. J Am Chem Soc, 2005, 127(15): 5490–5494

    Article  CAS  Google Scholar 

  36. Maurus J K, Bird G R. Circular dichroism of sensitizing dye aggregates. J Phys Chem, 1972, 76(21): 2982–2986

    Article  CAS  Google Scholar 

  37. Borovkov V V, Lintuluoto J M, Fujiki M, Inoue Y. Temperature effect on supramolecular chirality induction in bis(zinc porphyrin). J Am Chem Soc, 2000, 122(18): 4403–4407

    Article  CAS  Google Scholar 

  38. Nagai K, Maeda K, Takeyama Y, Sato T, Yashima E, Temperature- induced chiroptical changes in a helical poly(phenylacetylene) bearing N,N-diisopropyl aminomethyl groups with chiral acids in water. Chem Asian J, 2007, 2(15): 1314–1321

    Article  CAS  Google Scholar 

  39. Katzenelson O, Zabrodsky Hel-Or H, Avnir D. Chirality of large random supramolecular structures. Chem Eur J, 1996, 2(2): 174–182

    Article  CAS  Google Scholar 

  40. Katzenelson O, Avnir D. Quantitative chirality/enantioselectivity relations in large random supramolecular structures. Chem Eur J, 2000, 6(8): 1346–1354

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Graduate University of Chinese Academy of Sciences, Beijing, 100049, China

    LiXi Zeng, YuJian He, ZhiFeng Dai, Jian Wang & CaiQi Wang

  2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, China

    YuJian He

  3. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou, 215123, China

    YongGang Yang

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  1. LiXi Zeng
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  2. YuJian He
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  4. Jian Wang
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Correspondence to YuJian He.

Additional information

Supported by the National Natural Science Foundation of China (Grant Nos. 20571085, 20604033 & 20877099), the Fund of the State Key Laboratory of Natural and Biomimetic Drugs (Grant No. 20080208), Graduate University of Chinese Academy of Sciences (Grant No. 2007-2009) and Jiangsu Provincial Key Laboratory of Organic Chemistry Foundation and Natural Science Foundation of Jiangsu Province (Grant No. BK2007047).

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Zeng, L., He, Y., Dai, Z. et al. Chiral assembly of achiral pseudoisocyanine with D- and L-phenylalanine. Sci. China Ser. B-Chem. 52, 1227–1234 (2009). https://doi.org/10.1007/s11426-009-0115-y

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  • DOI: https://doi.org/10.1007/s11426-009-0115-y

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