Cellulose

, Volume 25, Issue 4, pp 2191–2203 | Cite as

Electronic and optical properties of chromophores from bacterial cellulose

Original Paper

Abstract

We report a systematic computational investigation on the electronic and optical properties of the principal chromophores found in bacterial cellulose (BC). In particular, we focus on the three chromophoric leading structures that were isolated from aged BC (1) 2,5-dihydroxy-[1,4]benzoquinone (2) 5,8-dihydroxy-[1,4]naphthoquinone and (3) 2,5-dihydroxyacetophenone. For the isolated molecules we performed all-electrons density functional theory (DFT) and time dependent DFT calculations with a localized Gaussian basis set and the hybrid exchange correlation functional B3LYP. We quantified key molecular properties relevant as electron affinities, ionization energies, quasi-particle energy gaps, optical absorption spectra, and exciton binding energies. We address moreover the impact of the solvent on the optical properties of the above systems using starting configurations obtained after classical molecular dynamics simulations in water. Our results could be of importance to comprehend the mechanisms underlying the processes of degradation of BC, which are of fundamental relevance for cultural heritage applications.

Keywords

Bacterial cellulose Chromophores Electronic properties Optical properties Density functional theory Cultural heritage 

Notes

Acknowledgments

The authors acknowledge the use of computational resources of CRS4 with special thanks to the high performance computing staffs. GC and RC acknowledge partial financial support from IDEA-AISBL Bruxelles. GC also acknowledges partial financial support from Progetto biennale d’Ateneo UniCa/FdS/RAS(Legge Regionale 07/08/2007 Annualità 2016) “Multiphysics theoretical approach to Thermoelectricity”. The authors thank A. Mosca Conte for introducing the topic of research and initial discussions.

Supplementary material

10570_2018_1728_MOESM1_ESM.docx (2.3 mb)
The absorption spectrum for the molecules expressed in oscillatory strength (Figs. S1–S4). Comparison between bond distance of the molecules after classical geometry optimization in vacuum and for the solvated conformer obtained from MD simulation in water (Tables S1–S4). In Table S5, detailed comparison among the absorption spectra of the three most probable conformers of molecule C extracted from MD simulations in water. (DOCX 2341 kb)

References

  1. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652.  https://doi.org/10.1063/1.464913 CrossRefGoogle Scholar
  2. Brown AJ (1886) XLIII—on an acetic ferment which forms cellulose. J Chem Soc Trans 49:432–439.  https://doi.org/10.1039/ct8864900432 CrossRefGoogle Scholar
  3. Cappellini G, Malloci G, Mulas G (2009) Electronic excitations of oligoacenes: a time dependent density functional theory study. Superlattices Microstruct 46:14–18.  https://doi.org/10.1016/j.spmi.2008.12.019 CrossRefGoogle Scholar
  4. Cardia R, Malloci G, Mattoni A, Cappellini G (2014) Effects of TIPS-functionalization and perhalogenation on the electronic, optical, and transport properties of angular and compact dibenzochrysene. J Phys Chem A 118:5170–5177.  https://doi.org/10.1021/jp502022t CrossRefGoogle Scholar
  5. Cardia R, Cappellini G, Pinna E, Tiddia MV, Mula G (2016a) Optical and electronic properties of monomers of eumelanin: a DFT and TD-DFT computational study. Optics and Photonics Journal 06:41–47.  https://doi.org/10.4236/opj.2016.68B008 CrossRefGoogle Scholar
  6. Cardia R, Malloci G, Rignanese GM, Blase X, Molteni E, Cappellini G (2016b) Electronic and optical properties of hexathiapentacene in the gas and crystal phases. Physical Review B.  https://doi.org/10.1103/physrevb.93.235132 Google Scholar
  7. Case DA et al (2005) The Amber biomolecular simulation programs. J Comput Chem 26:1668–1688.  https://doi.org/10.1002/jcc.20290 CrossRefGoogle Scholar
  8. Cavka A, Guo X, Tang S-J, Winestrand S, Jönsson LJ, Hong F (2013) Production of bacterial cellulose and enzyme from waste fiber sludge. Biotechnol Biofuels 6:25.  https://doi.org/10.1186/1754-6834-6-25 CrossRefGoogle Scholar
  9. ChemAxon (2017) http://www.chemaxon.com. Accessed 05 June 2017
  10. Conte AM, Pulci O, Misiti MC, Lojewska J, Teodonio L, Violante C, Missori M (2014) Visual degradation in Leonardo da Vinci’s iconic self-portrait: a nanoscale study. Appl Phys Lett 104:224101.  https://doi.org/10.1063/1.4879838 CrossRefGoogle Scholar
  11. Corsaro C, Mallamace D, Łojewska J, Mallamace F, Pietronero L, Missori M (2013) Molecular degradation of ancient documents revealed by 1H HR-MAS NMR spectroscopy. Sci Rep.  https://doi.org/10.1038/srep02896 Google Scholar
  12. Delogu GL et al (2016) 2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: synthesis, biological activity and molecular modeling. Biorg Med Chem Lett 26:2308–2313.  https://doi.org/10.1016/j.bmcl.2016.03.039 CrossRefGoogle Scholar
  13. Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714–3717.  https://doi.org/10.1021/jm000942e CrossRefGoogle Scholar
  14. Foster ME, Wong BM (2012) Nonempirically tuned range-separated DFT accurately predicts both fundamental and excitation gaps in DNA and RNA nucleobases. J Chem Theory Comput 8:2682–2687.  https://doi.org/10.1021/ct300420f CrossRefGoogle Scholar
  15. Grande CJ, Torres FG, Gomez CM, Troncoso OP, Canet-Ferrer J, Martínez-Pastor J (2009) Development of self-assembled bacterial cellulose–starch nanocomposites. Mater Sci Eng, C 29:1098–1104.  https://doi.org/10.1016/j.msec.2008.09.024 CrossRefGoogle Scholar
  16. Hogan C, Palummo M, Gierschner J, Rubio A (2013) Correlation effects in the optical spectra of porphyrin oligomer chains: exciton confinement and length dependence. J Chem Phys 138:024312.  https://doi.org/10.1063/1.4773582 CrossRefGoogle Scholar
  17. Humphrey W, Dalke A, Schulten K (1996) VMD: visual molecular dynamics. J Mol Graph 14(33–38):27–38Google Scholar
  18. Jensen F (2017) Introduction to computational chemistry, 3rd edn. Wiley, New YorkGoogle Scholar
  19. Jonas R, Farah LF (1998) Production and application of microbial cellulose. Polym Degradation Stab 59:101–106.  https://doi.org/10.1016/s0141-3910(97)00197-3 CrossRefGoogle Scholar
  20. Jones RO, Gunnarsson O (1989) The density functional formalism, its applications and prospects. Rev Mod Phys 61:689–746.  https://doi.org/10.1103/revmodphys.61.689 CrossRefGoogle Scholar
  21. Jorgensen WL, Chandrasekhar J, Madura JD, Impey RW, Klein ML (1983) Comparison of simple potential functions for simulating liquid water. J Chem Phys 79:926–935.  https://doi.org/10.1063/1.445869 CrossRefGoogle Scholar
  22. Kohn W (1999) Nobel lecture: electronic structure of matter—wave functions and density functionals. Rev Mod Phys 71:1253–1266.  https://doi.org/10.1103/revmodphys.71.1253 CrossRefGoogle Scholar
  23. Kucińska-Lipka J, Gubanska I, Janik H (2015) Bacterial cellulose in the field of wound healing and regenerative medicine of skin: recent trends and future prospectives. Polym Bull 72:2399–2419.  https://doi.org/10.1007/s00289-015-1407-3 CrossRefGoogle Scholar
  24. Kumar A et al (2013) Identification of calcium binding sites on calsequestrin 1 and their implications for polymerization. Mol BioSyst 9:1949.  https://doi.org/10.1039/c3mb25588c CrossRefGoogle Scholar
  25. Kumar A, Melis P, Genna V, Cocco E, Marrosu MG, Pieroni E (2014) Antigenic peptide molecular recognition by the DRB1–DQB1 haplotype modulates multiple sclerosis susceptibility. Mol BioSyst 10:2043–2054.  https://doi.org/10.1039/c4mb00203b CrossRefGoogle Scholar
  26. Kumar A, Sechi LA, Caboni P, Marrosu MG, Atzori L, Pieroni E (2015) Dynamical insights into the differential characteristics of Mycobacterium avium subsp. paratuberculosis peptide binding to HLA-DRB1 proteins associated with multiple sclerosis. New J Chem 39:1355–1366.  https://doi.org/10.1039/c4nj01903b CrossRefGoogle Scholar
  27. Lee C, Yang W, Parr RG (1988) Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density. Physical Review B 37:785–789.  https://doi.org/10.1103/PhysRevB.37.785 CrossRefGoogle Scholar
  28. Levin VA (1980) Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability. J Med Chem 23:682–684.  https://doi.org/10.1021/jm00180a022 CrossRefGoogle Scholar
  29. Malloci G, Cappellini G, Mulas G, Satta G (2004) Quasiparticle effects and optical absorption in small fullerenelike GaP clusters. Physical Review B.  https://doi.org/10.1103/physrevb.70.205429 Google Scholar
  30. Malloci G, Cappellini G, Mulas G, Mattoni A (2011) Electronic and optical properties of families of polycyclic aromatic hydrocarbons: a systematic (time-dependent) density functional theory study. Chem Phys 384:19–27.  https://doi.org/10.1016/j.chemphys.2011.04.013 CrossRefGoogle Scholar
  31. Marques MAL, Gross EKU (2004) Time-dependent density functional theory. Annu Rev Phys Chem 55:427–455.  https://doi.org/10.1146/annurev.physchem.55.091602.094449 CrossRefGoogle Scholar
  32. Missori M et al (2014) Optical response of strongly absorbing inhomogeneous materials: application to paper degradation. Physical Review B.  https://doi.org/10.1103/physrevb.89.054201 Google Scholar
  33. Molinspiration (2017) http://molinspiration.com/cgi-bin/properties. Accessed 09 June 2017
  34. Molteni E, Cappellini G, Onida G, Fratesi G (2017) Optical properties of organically functionalized silicon surfaces: uracil-like nucleobases on Si(001). Physical Review B.  https://doi.org/10.1103/physrevb.95.075437 Google Scholar
  35. Nishiyama Y (2009) Structure and properties of the cellulose microfibril. J Wood Sci 55:241–249.  https://doi.org/10.1007/s10086-009-1029-1 CrossRefGoogle Scholar
  36. O’Boyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR (2011) Open babel: an open chemical toolbox. J Cheminform 3:33.  https://doi.org/10.1186/1758-2946-3-33 CrossRefGoogle Scholar
  37. Okiyama A, Motoki M, Yamanaka S (1992) Bacterial cellulose II. Processing of the gelatinous cellulose for food materials. Food Hydrocolloids 6:479–487.  https://doi.org/10.1016/s0268-005x(09)80033-7 CrossRefGoogle Scholar
  38. Perdew JP, Burke K, Ernzerhof M (1996) Generalized gradient approximation made simple. Phys Rev Lett 77:3865–3868.  https://doi.org/10.1103/PhysRevLett.77.3865 CrossRefGoogle Scholar
  39. Phillips JC et al (2005) Scalable molecular dynamics with NAMD. J Comput Chem 26:1781–1802.  https://doi.org/10.1002/jcc.20289 CrossRefGoogle Scholar
  40. Rosenau T et al (2014) Chromophores in cellulosics, XI: isolation and identification of residual chromophores from bacterial cellulose. Cellulose 21:2271–2283.  https://doi.org/10.1007/s10570-014-0289-0 CrossRefGoogle Scholar
  41. Schedl A, Korntner P, Zweckmair T, Henniges U, Rosenau T, Potthast A (2016) Detection of cellulose-derived chromophores by ambient ionization-MS. Anal Chem 88:1253–1258.  https://doi.org/10.1021/acs.analchem.5b03646 CrossRefGoogle Scholar
  42. Shah J, Malcolm Brown R (2004) Towards electronic paper displays made from microbial cellulose. Appl Microbiol Biotechnol 66:352–355.  https://doi.org/10.1007/s00253-004-1756-6 CrossRefGoogle Scholar
  43. Shoda M, Sugano Y (2005) Recent advances in bacterial cellulose production. Biotechnol Bioprocess Eng 10:1–8.  https://doi.org/10.1007/bf02931175 CrossRefGoogle Scholar
  44. Svensson A, Nicklasson E, Harrah T, Panilaitis B, Kaplan DL, Brittberg M, Gatenholm P (2005) Bacterial cellulose as a potential scaffold for tissue engineering of cartilage. Biomaterials 26:419–431.  https://doi.org/10.1016/j.biomaterials.2004.02.049 CrossRefGoogle Scholar
  45. Tabuchi M (2007) Nanobiotech versus synthetic nanotech? Nat Biotechnol 25:389–390.  https://doi.org/10.1038/nbt0407-389 CrossRefGoogle Scholar
  46. Torres F, Commeaux S, Troncoso O (2012) Biocompatibility of bacterial cellulose based biomaterials journal of functional. Biomaterials 3:864–878.  https://doi.org/10.3390/jfb3040864 Google Scholar
  47. Ullah H, Santos HA, Khan T (2016) Applications of bacterial cellulose in food, cosmetics and drug delivery. Cellulose 23:2291–2314.  https://doi.org/10.1007/s10570-016-0986-y CrossRefGoogle Scholar
  48. Valiev M et al (2010) NWChem: a comprehensive and scalable open-source solution for large scale molecular simulations. Comput Phys Commun 181:1477–1489.  https://doi.org/10.1016/j.cpc.2010.04.018 CrossRefGoogle Scholar
  49. Vandamme EJ, De Baets S, Vanbaelen A, Joris K, De Wulf P (1998) Improved production of bacterial cellulose and its application potential. Polym Degradation Stab 59:93–99.  https://doi.org/10.1016/s0141-3910(97)00185-7 CrossRefGoogle Scholar
  50. Wang J, Wolf RM, Caldwell JW, Kollman PA, Case DA (2004) Development and testing of a general amber force field. J Comput Chem 25:1157–1174.  https://doi.org/10.1002/jcc.20035 CrossRefGoogle Scholar
  51. Warren SG (1984) Optical constants of ice from the ultraviolet to the microwave. Appl Opt 23:1206.  https://doi.org/10.1364/ao.23.001206 CrossRefGoogle Scholar
  52. Warren SG, Brandt RE (2008) Optical constants of ice from the ultraviolet to the microwave: a revised compilation. J Geophys Res.  https://doi.org/10.1029/2007jd009744 Google Scholar
  53. Yano H, Sugiyama J, Nakagaito AN, Nogi M, Matsuura T, Hikita M, Handa K (2005) Optically transparent composites reinforced with networks of bacterial nanofibers. Adv Mater 17:153–155.  https://doi.org/10.1002/adma.200400597 CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  • Amit Kumar
    • 1
    • 2
  • Roberto Cardia
    • 3
    • 4
  • Giancarlo Cappellini
    • 3
    • 4
  1. 1.Department of Mechanical, Chemical and Materials EngineeringUniversity of CagliariCagliariItaly
  2. 2.Biosciences SectorCenter for Advanced Study Research and Development in Sardinia (CRS4)PulaItaly
  3. 3.Department of PhysicsUniversity of Cagliari, Cittadella UniversitariaMonserrato, CagliariItaly
  4. 4.CNR-IOMUniversity of Cagliari, Cittadella UniiversitariaMonserrato, CagliariItaly

Personalised recommendations