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Quinone—Bodipy H-bonding interaction over π-stacking in toluene

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Abstract

Quinone type compounds (o-chloranil, p-chloranil and DDQ) demonstrate excellent H-bonding interactions with a meso-phenol Bodipy dye (1) in both ground and excited state in a non-polar toluene medium. The spectroscopic detection of isosbestic absorption occurs with both quinones and fullerenes, but only quinones form isoemissive complexes with dye 1. 1H NMR study and Monte Carlo global minima searching justified the above mentioned results with efficiency.

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Notes and references

  1. M. Olofsson, S. Kalinin, J. Zdunek, M. Oliveberg, L. B.-A. Johansson, Tryptophan–BODIPY: A versatile donor–acceptor pair for probing generic changes of intraprotein distances, Phys. Chem. Chem. Phys., 2006 8, 3130.

    Article  CAS  PubMed  Google Scholar 

  2. W. Zhu, W. Li, C. Wang, J. Cui, H. Yang, Y. Jiang and G. Li, CB[8]-based rotaxane as a useful platform for sensitive detection and discrimination of explosives, J. Chem. Sci., 2013 4, 3583.

    Article  CAS  Google Scholar 

  3. A. Coskun, J. M. Spruell, G. Barin, W. R. Dichtel, A. H. Flood, Y. Y. Botros, J. Fraser Stoddart, High hopes: can molecular electronics realise its potential?, J. Chem. Soc. Rev., 2012 41, 4827.

    Article  CAS  Google Scholar 

  4. S. J. Cantrill, A. R. Pease and J. F. Stoddart, A molecular meccano kit, J. Chem. Soc., Dalton Trans., 2000, 3715.

    Google Scholar 

  5. J. Rebek and D. Nemeth, Molecular recognition: ionic and aromatic stacking interactions bind complementary functional groups in a molecular cleft, J. Am. Chem. Soc., 1986 108, 5637.

    Article  CAS  Google Scholar 

  6. S. K. Burley and G. A. Petsko, Dimerization energetics of benzene and aromatic amino acid side chains, J. Am. Chem. Soc., 1986 108, 7995.

    Article  CAS  Google Scholar 

  7. A. D. Hamilton and D. V. Engen, Induced fit in synthetic receptors: nucleotide base recognition by a molecular hinge, J. Am. Chem. Soc., 1987 109, 5035.

    Article  CAS  Google Scholar 

  8. S. C. Zimmerman and C. M. Vanzyl, Rigid molecular tweezers: synthesis, characterization, and complexation chemistry of a diacridine, J. Am. Chem. Soc., 1987 109, 7894.

    Article  CAS  Google Scholar 

  9. J. C. Nelson, J. G. Saven, J. S. Moore and P. G. Wolynes, Solvophobically Driven Folding of Nonbiological Oligomers, Science, 1997 277, 1793.

    Article  CAS  PubMed  Google Scholar 

  10. C. A. Hunter, Arene—Arene Interactions: Electrostatic or Charge Transfer?, Angew. Chem., Int. Ed. Engl., 1993 32, 1584.

    Article  Google Scholar 

  11. C. A. Hunter, Meldola Lecture. The role of aromatic interactions in molecular recognition, Chem. Soc. Rev., 1994 23, 101.

    Article  CAS  Google Scholar 

  12. S. B. Ferguson and F. Diederich, Electron Donor–Acceptor Interactions in Host–Guest Complexes in Organic Solutions, Angew. Chem., Int. Ed. Engl., 1986 25, 1127.

    Article  Google Scholar 

  13. M. Nishio and M. Hirota, CH/p interaction: Implications in organic chemistry, Tetrahedron, 1989 45, 7201.

    Article  CAS  Google Scholar 

  14. S. Ghosh, T. Chaudhuri and C. Mukhopadhyay, The new threading system 2-benzyl-5,6-dimethyl-1H-benzo[d]imidazolium–dibenzo-24-crown-8: a model for Monte Carlo calculations incorporating an anion for the first time in threaded structures, RSC Adv., 2014 4, 18835.

    Article  CAS  Google Scholar 

  15. S. Ghosh, T. Chaudhuri, A. M. Schmiedekamp, E. Padmanaban and C. Mukhopadhyay, A 2,2’-bis(benzimidazolium)-dibenzo[24]crown[8] rigid pseudorotaxane system, Tetrahedron, 2014 70, 6885.

    Article  CAS  Google Scholar 

  16. M. Kotera, J. M. Lehn and J. P. Vigneron, Self-assembled supramolecular rigid rods, J. Chem. Soc., Chem. Commun., 1994, 197.

    Google Scholar 

  17. R. P. Sijbesma and E. W. Meijer, Self-assembly of well-defined structures by hydrogen bonding, Curr. Opin. Colloid Interface Sci., 1999 4, 24.

    Article  CAS  Google Scholar 

  18. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997.

    Google Scholar 

  19. A. Ben-Naim, Hydrophobic Interactions, Plenum Press, New York & London, 1980.

    Book  Google Scholar 

  20. A. C. Bhasikuttan, J. Mohanty, W. M. Nau and H. Pal, Efficient fluorescence enhancement and cooperative binding of an organic dye in a supra-biomolecular host-protein assembly, Angew. Chem., Int. Ed., 2007 46, 4120.

    Article  CAS  Google Scholar 

  21. A. G. Street and S. L. Mayo, Intrinsic b-sheet propensities result from van der Waals interactions between side chains and the local backbone, Proc. Natl. Acad. Sci. U. S. A., 1999 96, 9074.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. K. Ohta, M. Ikejima, M. Moriya, H. Hasebe and I. Yamamoto, Disk-like liquid crystals of transition metal complexes. Part 20 Pursuit of chemistry to directly visualize van der Waals interactions, J. Mater. Chem., 1998 8, 1971.

    Article  Google Scholar 

  23. A. Loudet and K. Burgess, BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties, Chem. Rev., 2007 107, 4891.

    Article  CAS  PubMed  Google Scholar 

  24. N. Boens, V. Leen and W. Dehaen, Fluorescent indicators based on BODIPY, Chem. Soc. Rev., 2012 41, 1130.

    Article  CAS  PubMed  Google Scholar 

  25. A. Kamkaew, S. H. Lim, H. B. Lee, L. V. Kiew, L. Y. Chung and K. Burgess, BODIPY dyes in photodynamic therapy, Chem. Soc. Rev., 2013 42, 77.

    Article  CAS  PubMed  Google Scholar 

  26. H. Lu, J. Mack, Y. Yanga and Z. Shen, Structural modification strategies for the rational design of red/NIR region BODIPYs, Chem. Soc. Rev., 2014 43, 4778.

    Article  CAS  PubMed  Google Scholar 

  27. A. Bessette and G. S. Hanan, Design, synthesis and photophysical studies of dipyrromethene-based materials: insights into their applications in organic photovoltaic devices, Chem. Soc. Rev., 2014 43, 3342.

    Article  CAS  PubMed  Google Scholar 

  28. S. Mula, A. Roy, M. Banerjee, T. Chaudhuri, K. Dasgupta and S. Chattopadhyay, Design and Development of a New Pyrromethene Dye with Improved Photostability and Lasing Efficiency: Theoretical Rationalization of Photophysical and Photochemical Properties, J. Org. Chem., 2008 73, 2146.

    Article  CAS  PubMed  Google Scholar 

  29. S. Mula, K. Elliott, A. Harriman and R. Ziessel, Energy Transfer by Way of an Exciplex Intermediate in Flexible Boron Dipyrromethene-Based Allosteric Architectures, J. Phys. Chem. A, 2010 114, 10515.

    Article  CAS  PubMed  Google Scholar 

  30. N. Shivran, S. Mula, T. K. Ghanty and S. Chattopadhyay, Steric Strain Release-Directed Regioselective Functionalization of meso-Methyl Bodipy Dyes, Org. Lett., 2011 13, 5870.

    Article  CAS  PubMed  Google Scholar 

  31. M. Gupta, S. Mula, M. Tyagi, T. K. Ghanty, S. Murudkar, A. K. Ray and S. Chattopadhyay, Rational Design of Boradiazaindacene (BODIPY)-Based Functional Molecules, Chem.–Eur. J., 2013 19, 17766.

    Article  CAS  PubMed  Google Scholar 

  32. K. K. Jagtap, N. Shivran, S. Mula, D. B. Naik, S. K. Sarkar, T. Mukherjee, D. K. Maity and A. K. Ray, Change of Boron Substitution Improves the Lasing Performance of Bodipy Dyes: A Mechanistic Rationalisation, Chem.–Eur. J., 2013 19, 702.

    Article  CAS  PubMed  Google Scholar 

  33. F. Camerel, L. Bonardi, M. Schmutz and R. Ziessel, Highly Luminescent Gels and Mesogens Based on Elaborated Borondipyrromethenes., J. Am. Chem. Soc., 2006 128, 4548.

    Article  CAS  PubMed  Google Scholar 

  34. S. Frein, F. Camerel, R. Ziessel, J. Barberá and R. Deschenaux, Highly Fluorescent Liquid-Crystalline Dendrimers Based on Borondipyrromethene Dyes, Chem. Mater., 2009 121, 3950.

    Article  CAS  Google Scholar 

  35. V. Lazic, M. Jurkovic, T. Jednacak, T. Hrenar, J. P. Vukovic and P. Novak, Intra- and intermolecular hydrogen bonding in acetylacetone and benzoylacetone derived enaminone derivatives, J. Mol. Struct., 2015, 1079, 243.

    Article  CAS  Google Scholar 

  36. G. Chang, W. C. Guida and W. C. Still, An internal-coordinate Monte Carlo method for searching conformational space, J. Am. Chem. Soc., 1989 111, 4379.

    Article  CAS  Google Scholar 

  37. J. Kong, C. A. White, A. I. Krylov, C. D. Sherrill, R. D. Adamson, T. R. Furlani, M. S. Lee, A. M. Lee, S. R. Gwaltney, T. R. Adams, C. Ochsenfeld, A. T. B. Gilbert, G. S. Kedziora, V. A. Rassolov, D. R. Maurice, N. Nair, Y. Shao, N. A. Besley, P. E. Maslen, J. P. Dombroski, H. Daschel, W. Zhang, P. P. Korambath, J. Baker, E. F. C. Byrd, T. V. Voorhis, M. Oumi, S. Hirata, C. P. Hsu, N. Ishikawa, J. Florian, A. Warshel, B. G. Johnson, P. M. W. Gill, M. Head-Gordon and J. A. Pople, Q-Chem 2.0: a high-performance ab initio electronic structure program package, J. Comput. Chem., 2000 21, 1532.

    Article  CAS  Google Scholar 

  38. S. J. Cantrill, A. R. Pease and J. F. Stoddart, J. Chem. Soc., Dalton Trans., 2000, 3715.

    Google Scholar 

  39. A. C. Bhasikuttan, J. Mohanty, W. M. Nau and H. Pal, Angew. Chem., Int. Ed., 2007 46, 4120.

    Article  CAS  Google Scholar 

  40. R. Baer, E. Livshits and U. Salzner, Annu. Rev. Phys. Chem., 2010 61, 85.

    Article  CAS  PubMed  Google Scholar 

  41. S. S. Velu, F. Di Meo, P. Trouillas, J.-C. Sancho-Garcia and J.-F. F. Weber, J. Nat. Prod., 2013 76, 538.

    Article  CAS  PubMed  Google Scholar 

  42. D. S. Sholl and J. A. Steckel, Density Function Theory A Practical Introduction, John Wiley & Sons., 2009, Ch. 9, p. 1.

    Book  Google Scholar 

  43. G. Chang, W. C. Guida and W. C. Still, J. Am. Chem. Soc., 1989 111, 4379.

    Article  CAS  Google Scholar 

  44. J. Kong, C. A. White, A. I. Krylov, C. D. Sherrill, R. D. Adamson, T. R. Furlani, M. S. Lee, A. M. Lee, S. R. Gwaltney, T. R. Adams, C. Ochsenfeld, A. T. B. Gilbert, G. S. Kedziora, V. A. Rassolov, D. R. Maurice, N. Nair, Y. Shao, N. A. Besley, P. E. Maslen, J. P. Dombroski, H. Daschel, W. Zhang, P. P. Korambath, J. Baker, E. F. C. Byrd, T. VanVoorhis, M. Oumi, S. Hirata, C. P. Hsu, N. Ishikawa, J. Florian, A. Warshel, B. G. Johnson, P. M. W. Gill, M. Head-Gordon and J. A. Pople, J. Comput. Chem., 2000 21, 1532.

    Article  CAS  Google Scholar 

  45. T. Chaudhuri, S. Mula, S. Chattopadhyay and M. Banerjee, Photophysical properties of the 8-phenyl analogue of PM567: a theoretical rationalization, Spectrochim. Acta, Part A, 2010, 75, 739.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Dr Bhupendranath Dutta Smriti Mahavidyalaya, Burdwan, 713407, India

    Animesh Karmakar & Tandrima Chaudhuri

  2. Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India

    Soumyaditya Mula, Neelam Shivran & Subrata Chattopadhyay

  3. Department of Chemistry, The University of Burdwan, Golapbag, Burdwan, 713104, India

    Kalyan Ghosh & Manas Banerjee

Authors
  1. Animesh Karmakar
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  2. Soumyaditya Mula
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  3. Kalyan Ghosh
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  4. Tandrima Chaudhuri
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  5. Neelam Shivran
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  7. Subrata Chattopadhyay
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Corresponding author

Correspondence to Tandrima Chaudhuri.

Additional information

Electronic supplementary information (ESI) available: Copies of NMR spectra, isosbestic and iso-emissive spectra of all five systems and MC conformers coordinates are given. See DOI: 10.1039/c5pp00035a

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Karmakar, A., Mula, S., Ghosh, K. et al. Quinone—Bodipy H-bonding interaction over π-stacking in toluene. Photochem Photobiol Sci 14, 1207–1212 (2015). https://doi.org/10.1039/c5pp00035a

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  • DOI: https://doi.org/10.1039/c5pp00035a

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