Skip to main content
SpringerLink
Log in

Calixarene building block bis(2-hydroxyphenyl)methane (2HDPM) and hydrogen-bonded 2HDPM-H2O complex in electronic excited state

  • Original Paper
  • Published:
Journal of Molecular Modeling Aims and scope Submit manuscript

Abstract

Intramolecular and intermolecular hydrogen bonding in electronic excited states of calixarene building blocks bis(2-hydroxyphenyl)methane (2HDPM) monomer and hydrogen-bonded 2HDPM-H2O complex were studied theoretically using the time-dependent density functional theory (TDDFT). Twenty-four stable conformations (12 pairs of enantiomers) of 2HDPM monomer have been found in the ground state. From the calculation results, the conformations 1a and 1b which both have an intramolecular hydrogen bond are the most stable ones. The infrared spectra of 2HDPM monomer and 2HDPM-H2O complex in ground state and S1 state were calculated. The stretching vibrational absorption band of O2 − H3 group in the monomer and complex disappeared in the S1 state. At the same time, a new strong absorption band appeared at the C=O stretching region. From the calculation of bond lengths, it indicates that the O2 − H3 bond is significantly lengthened in the S1 state. However, the C1 − O2 bond is drastically shortened upon electronic excitation to the S1 state and has the characteristics of C=O band. Furthermore, the intramolecular hydrogen bond O2 − H3 · · · O4 of the 2HDPM monomer and the intermolecular hydrogen bonds O2 − H3 · · · O7 and O7 − H9 · · · O4 of 2HDPM-H2O complex are all shortened and strengthened in the S1 state.

Intramolecular and intermolecular hydrogen bonding in electronic excited states of calixarene building blocks bis(2-hydroxyphenyl)methane (2HDPM) monomer and hydrogen-bonded 2HDPM-H2O complex were studied by TDDFT method

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Han K-L, Zhao G-J (2011) Hydrogen bonding and transfer in the excited state. John Wiley & Sons Ltd, Chichester, UK

  2. Sharif S, Fogle E, Toney MD, Denisov GS, Shenderovich IG, Buntkowsky G, Tolstoy PM, Huot MC, Limbach HH (2007) J Am Chem Soc 129:9558

    Article  CAS  Google Scholar 

  3. Yamada Y, Mikami N, Ebata T (2008) Proc Natl Acad Sci USA 105:12690

    Article  CAS  Google Scholar 

  4. Zhao G-J, Han K-L (2012) Acc Chem Res 45:404

    Article  CAS  Google Scholar 

  5. Kawanabe A, Furutani Y, Jung KH, Kandori H (2009) J Am Chem Soc 131:16439

    Article  CAS  Google Scholar 

  6. Ji SM, Yang J, Yang Q, Liu SS, Chen MD, Zhao JZ (2009) J Org Chem 74:4855

    Article  CAS  Google Scholar 

  7. Zhao GJ, Northrop BH, Stang PJ, Han KL (2010) J Phys Chem A 334 114:3418

    Google Scholar 

  8. Zhao GJ, Han KL (2010) Phys Chem Chem Phys 12:8914

    Article  CAS  Google Scholar 

  9. Desfrancois C, Carles S, Schermann JP (2000) Chem Rev 100:3943

    Article  CAS  Google Scholar 

  10. Zhao GJ, Yu F, Zhang MX, Northrop BH, Yang HB, Han KL, Stang PJ (2011) J Phys Chem A 115:6390

    Article  CAS  Google Scholar 

  11. Sakota K, Shimazaki Y, Sekiya H (2009) J Chem Phys 130:231105

    Article  Google Scholar 

  12. Djikaev YS, Ruckenstein E (2009) J Chem Phys 130:124713

    Article  CAS  Google Scholar 

  13. Chu TS, Zhang Y, Han KL (2006) Int Rev Phys Chem 25:201

    Article  CAS  Google Scholar 

  14. Zhao G-J, Han K-L, Stang PJ (2009) J Chem Theory Comput 5:1955

    Article  CAS  Google Scholar 

  15. Kearley GJ, Fillaux F, Baron MH, Bennington S, Tomkinson JA (1994) Science 264:1285

    Article  CAS  Google Scholar 

  16. Jimenez R, Fleming GR, Kumar PV, Maroncelli M (1994) Nature 369:471

    Article  CAS  Google Scholar 

  17. Yu F, Li P, Li G, Zhao GJ, Chu TS, Han KL (2011) J Am Chem Soc 133:11030

    Article  CAS  Google Scholar 

  18. Zhao GJ, Han KL (2008) Biophys J 94:38

    Article  CAS  Google Scholar 

  19. Zhao G, Northrop BH, Han K, Stang P (2010) J Phys Chem A 114:9007

    Article  CAS  Google Scholar 

  20. Zhao GJ, Han KL (2007) J Chem Phys 127:024306

    Article  Google Scholar 

  21. Han KL, He GZ (2007) J Photochem Photobiol C: Photochem Rev 8:55

    Article  CAS  Google Scholar 

  22. Zhao GJ, Han KL (2007) J Phys Chem A 111:9218

    Google Scholar 

  23. Zhao GJ, Han KL (2008) ChemPhysChem 9:1842

    Article  CAS  Google Scholar 

  24. Zhao G, Liu J, Zhou L, Han KL (2007) J Phys Chem B 111:8940

    Article  CAS  Google Scholar 

  25. Zhao GJ, Han KL (2008) J Comput Chem 29:2010

    Article  CAS  Google Scholar 

  26. Zhao G, Chen R, Sun M, Liu J, Li G, Gao Y, Han K, Yang X, Sun L (2008) Chem Eur J 14:6935

    Article  CAS  Google Scholar 

  27. Zhao G, Han KL (2009) J Phys Chem A 113:14329

    Article  CAS  Google Scholar 

  28. Zhao GJ, Han KL (2007) J Phys Chem A 111:2469

    Article  CAS  Google Scholar 

  29. Liu Y, Zhao G, Li G, Han KL (2010) J Photochem Photobiol A: Chem 209:181

    Article  CAS  Google Scholar 

  30. Zhao G-J, Han K-L (2008) Hydrogen bonding effects on the photochemistry of chromophores in solution. In: Sánchez A, Gutierrez SJ (eds) Photochemistry research progress, Ch 5. Nova Science, New York

    Google Scholar 

  31. Gutsche C.D (1998) Calixarenes revistied. In: Stoddart JF (ed) Monographss in supramolucular chemistry. The Royal Society of Chemistry, Cambridge, UK

  32. Gutsche CD (1989) Calixarenes. In: Stoddart JF (ed) Monographss in supramolucular chemistry. The Royal Society of Chemistry, Cambridge, UK

  33. Katsyuba S, Chernova A, Schmutzler R, Grunenberg JJ (2002) Chem Soc, Perkin Trans 2:67

    Google Scholar 

  34. Pillsbury NR, Müller CW, Meerts WL, Plusquellic DF, Zwier TS (2009) J Phys, Chem. A 113:5000

    CAS  Google Scholar 

  35. Pillsbury NR, Müller CW, Zwier TS (2009) J Phys Chem A 113:5013

    Article  CAS  Google Scholar 

  36. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  37. Schäfer A, Huber C, Ahlrichs R (1994) J Chem Phys 100:5829

    Article  Google Scholar 

  38. Ahlrichs R, Bär M, Horn H, Kölmel C (1989) Chem Phys Lett 162:165

    Article  CAS  Google Scholar 

  39. Zhang MX, Zhao GJ (2012) ChemSusChem 5:879

    Article  CAS  Google Scholar 

  40. Treutler O, Ahlrichs RJ (1995) Chem Phys 102:346

    CAS  Google Scholar 

  41. Furche F, Ahlrichs RJ (2002) Chem Phys 117:7433

    CAS  Google Scholar 

  42. Deglmann P, Furche FJ (2002) Chem Phys 117:9535

    CAS  Google Scholar 

  43. Xie Y, Schreiner P, Schleyer P, Schaefer HF (1997) J Am Chem Soc 119:1370

    Article  CAS  Google Scholar 

  44. Zhao G, Cheng C (2012) Amino Acids 43:557

    Article  CAS  Google Scholar 

  45. Weber P, Reimers JR (1999) J Phys Chem A 103:9830

    Article  CAS  Google Scholar 

  46. Wang S, Hao C, Gao Z, Chen J, Qiu J (2012) Chemosphere 88:33

    Article  CAS  Google Scholar 

  47. Wang S, Hao C, Gao Z, Chen J, Qiu J (2011) J Lumin 131:2279

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant Nos. 21036006 and 21137001; 20903094 and 20833008).

Author information

Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Key Laboratory of Industrial Ecology and Environmental Engineering (MOE), School of Environmental Science and Technology, Dalian University of Technology, Dalian, 116024, China

    Se Wang, Ce Hao, Zhanxian Gao, Jingwen Chen & Jieshan Qiu

  2. State Key Laboratory of Molecular Reaction Dynamics and Center for Theoretical and Computational Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China

    Se Wang

Authors
  1. Se Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ce Hao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhanxian Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jingwen Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jieshan Qiu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ce Hao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, S., Hao, C., Gao, Z. et al. Calixarene building block bis(2-hydroxyphenyl)methane (2HDPM) and hydrogen-bonded 2HDPM-H2O complex in electronic excited state. J Mol Model 19, 1913–1918 (2013). https://doi.org/10.1007/s00894-012-1710-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00894-012-1710-y

Keywords

Search

Navigation