Laser-induced fluorescence (LIF) of lignin and lignin model compounds in Raman spectroscopy

Holzforschung

Volumn 67, Issue 5, 2013, Pages 531-538

  Lähdetie, Anni ^a   Nousiainen, Paula ^b   Sipilä, Jussi ^b   Tamminen, Tarja ^c   Jääskeläinen, Anna Stiina ^c  

^a AALTO UNIVERSITY   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

^c VTT TECHNICAL RESEARCH CENTRE OF FINLAND   (Finland)

Author keywords

5 5 linkage; dibenzodioxocin; fluorescence spectroscopy; laser induced fluorescence (LIF); lignin; Raman spectroscopy

Indexed keywords

BACKGROUND SIGNALS; CONFORMATIONAL ASPECTS; DIBENZODIOXOCIN; EXCITATION WAVELENGTH; LASER INDUCED FLUORESCENCE; LIGNIN MODEL COMPOUND; LIGNIN STRUCTURE; STRUCTURAL INFORMATION;

CONFORMATIONS; FLUORESCENCE SPECTROSCOPY; LASER PRODUCED PLASMAS; LIGNIN; RAMAN SPECTROSCOPY;

WOOD;

LIGNINS; RAMAN SPECTROSCOPY; WOOD;

EID: 84882953490     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/hf-2012-0177     Document Type: Article

References (61)

1. Achyuthan, K.E., Adams, P.D., Datta, S., Simmons, B.A., Singh, A.K. (2010) Hitherto unrecognized fluorescence properties of coniferyl alcohol. Molecules 15:1645- 1667.
2. Agarwal, U.P. (1999) An overview of Raman spectroscopy as applied to lignocellulosic materials. In: Advances in Lignocellulosics Characterization. Ed. Argyropoulos, D.S. Tappi Press, Atlanta, GA, pp. 201- 225.
3. Agarwal, U.P., Atalla, R.H. (1995) Raman spectroscopy. In: Surface Analysis of Paper. Eds. Conners, T.E., Banerjee, S. CRC Press, Boca Raton, FL, pp. 152-181.
4. Agarwal, U.P., Ralph, S.A. (2008) Determination of ethylenic residues in wood and TMP of spruce by FT-Raman spectroscopy. Holzforschung 62:667-675.
5. Agarwal, U.P., Terashima, N. (2003) FT-Raman study of dehydrogenation polymer (DHP) lignins. In: 12th ISWPC International Symposium on Wood and Pulping Chemistry, Madison, WI, June 9-12.
6. Albinsson, B., Li, S., Lundquist, K., Stomberg, R. (1999) The origin of lignin fluorescence. J. Mol. Struct. 508:19-27. (Pubitemid 29444679)
7. Atalla, R.H., Nagel, S.C. (1972) Laser-induced fluorescence in cellulose. J. Chem. Soc. Chem. Commun. 19:1049-1050.
8. Atalla, R.H., Agarwal, U.P., Bond J.S. (1992) Raman spectroscopy. In: Methods in Lignin Chemistry. Eds. Lin, S.Y., Dence, C.W. Springer-Verlag, Berlin, pp. 162-176.
9. Barsberg, S., Matousek, P., Towrie, M. (2005) Structural analysis of lignin by resonance Raman spectroscopy. Macromol. Biosci. 5:743-752. (Pubitemid 41232825)
10. Barsberg, S., Matousek, P., Towrie, M., Jørgensen, H., Felby, C. (2006) Lignin radicals in the plant cell wall probed by Kerr-gated resonance Raman spectroscopy. Biophys. J. 90:2978-2986.
11. Capanema, E.A., Balakshin, M.Y., Kadla, J.F. (2004) A comprehensive approach for quantitative lignin characterization by NMR spectroscopy. J. Agric. Food Chem. 52:1850-1860.
12. Dence, C.W. (1992) The determination of lignin. In: Methods in Lignin Chemistry. Eds. Lin, S.Y., Dence, C.W. Springer-Verlag, Berlin, pp. 33-61.
13. Elbs, K., Lerch, H. (1916)über dehyrdovanillin. J. Prakt. Chem. 98:1-9.
14. Fujimoto, A., Matsumoto, Y., Chang, H.M., Meshitsuka, G. (2005) Quantitative evaluation of milling effects on lignin structure during the isolation process of milled wood lignin. J. Wood Sci. 51:89-91.
15. Ganne-Chédeville, C., Jä äskeläinen, A-S, Froidevaux, J., Hughes, M., Navi, P (2012) Natural and artificial ageing of spruce wood as observed by FTIR-ATR and UVRR spectroscopy. Holzforschung 66:163-170.
16. Gardrat, C., Ruggiero, R., Hoareau, W., Nourmamode, A., Grelier, S., Siegmund, B., Castellan, A. (2004) Photochemical study of an o -ethyl dibenzodioxocin molecule as a model for the photodegradation of non-phenolic lignin units of lignocellulosics. J. Photochem. Photobiol. A. 167:111-120.
17. Gardrat, C., Ruggiero, R., Hoareau, W., Damigo, L., Nourmamode, A., Grelier, S., Castellan, A (2005) Photochemical study of 4-(4,9-dimethoxy-2,11-n -dipropyl-6,7-dihydro-5,8-dioxadibenzo[a, c ]cycloocten-6-yl)-2-methoxyphenol, a lignin model of phenolic dibenzodioxocin unit. J. Photochem. Photobiol. A. 169:261-269. (Pubitemid 40058024)
18. Gierlinger, N., Schwanninger, M. (2007) The potential of Raman microscopy and Raman imaging in plant research. Spectroscopy 21:69-89. (Pubitemid 47255967)
19. Glasser, W.G., Northey, R.A., Schultz, T.P. Lignin: Historical, Biological, and Materials Perspectives. American Chemical Society, Washington, DC, 2000.
20. Hamad, W.Y., Gurnagul, N., Gulati, D. (2012) Analysis of fibre deformation processes in high-consistency refining based on Raman microscopy and X-ray diffraction. Holzforschung 66:711-716.
21. Hänninen, T., Tukiainen, P., Svedström, K., Serimaa, R., Saranpä ä, P., Kontturi, E., Hughes, M., Vuorinen, T. (2012) Ultrastructural evaluation of compression wood-like properties of common juniper (Juniperus communis L). Holzforschung 66:389-395.
22. Hofrichter, M., Vares, K., Scheibner, K., Galkin, S., Sipila, J., Hatakka, A. (1999) Mineralization and solubilization of synthetic lignin by manganese peroxidases from Nematoloma frowardii and Phlebia radiata . J. Biotechnol. 67:217-228. (Pubitemid 29062892)
23. Horvath, L., Peszlen, I., Gierlinger, N., Peralta, P., Kelley, S., Csoka, L. (2012) Distribution of wood polymers within the cell wall of transgenic aspen imaged by Raman microscopy. Holzforschung 66:717-725.
24. Imai, Y., Kamon, K., Tajima, N., Kinuta, T., Sato, T., Kuroda, R., Matsubara, Y. (2010) Solid-state fluorescence property and crystal structure of biphenyl derivatives with carboxyl and n -alkyl groups. J. Lumines. 130:954-958.
25. Jä äskeläinen, A-S., Sun, Y., Argyropoulos, D., Tamminen, T., Hortling, B. (2003) The effect of isolation method on the chemical structure of residual lignin. Wood Sci. Technol. 37:91-102.
26. Jä äskeläinen, A-S., Saariaho, A-M., Vy örykk ä, J., Vuorinen, T., Matousek, P., Parker, A.W. (2006) Application of UV-Vis and resonance Raman spectroscopy to study bleaching and photoyellowing of thermomechanical pulps. Holzforschung 60:231-238.
27. Jä äskeläinen, A-S., Toikka, K., Lähdetie, A., Liitiä, T., Vuorinen, T. (2009) Reactions of aromatic structures in brightness reversion of fully-bleached eucalyptus kraft pulps. Holzforschung 63:278-281.
28. Karhunen, P. Studies on Syntheses and Reactions of Lignin Model Compounds with Biphenyl, Diaryl Ether und Dibenzodioxocin Structures. Dissertation, University of Helsinki, Espoo, 1999.
29. Karhunen, P., Rummakko, P., Sipilä, J., Brunow, G., Kilpeläinen, I. (1995a) The formation of dibenzodioxocin structures by oxidative coupling. A model reaction for lignin biosynthesis. Tetrahedron Lett. 36:4501-4504.
30. Karhunen, P., Rummakko, P., Sipilä, J., Brunow, G., Kilpeläinen, I. (1995b) Dibenzodioxocins; a novel type of linkage in softwood lignins. Tetrahedron Lett. 36:169-170.
31. Kratzl, K., Wagner, I. (1972) Model tests for condensation of lignin. 2. Complete methylation of lignins and models-condensation reactions of phenols with formaldehyde and xylose. Holzforschung Holzverwertung 24:56-61.
32. Kukkola, E.M., Koutaniemi, S., Pö ll änen, E., Gustafsson, M., Karhunen, P., Lundell, T.K., Saranpä ä, P., Kilpeläinen, I., Teeri, T.H., Fagerstedt, K.V. (2004) The dibenzodioxocin lignin substructure is abundant in the inner part of the secondary wall in Norway spruce and silver birch xylem. Planta 218:497-500. (Pubitemid 38154265)
33. Lähdetie, A., Liitiä, T., Tamminen, T., Jä äskeläinen, A-S. (2009a) Reflectance UV-Vis and UV resonance Raman spectroscopy in characterization of kraft pulps. BioResources 4:1600-1619.
34. Lähdetie, A., Liitiä, T., Tamminen, T., Pere, J., Jä äskeläinen, A-S. (2009b) Activation of thermomechanical pulp by laccases as studied by UV-Vis, UV resonance Raman and FTIR spectroscopy. 10th EWLP, Stockholm, Sweden, August 25-28, 2008. Holzforschung 63:745-750.
35. Lakowicz, J.R., Masters, B.R. Principles of Fluorescence Spectroscopy. Springer, New York (NY), 2008.
36. Lundquist, K., Josefsson, B., Nyquist, G. (1978) Analysis of lignin products by fluorescence spectroscopy. Holzforschung 32:27-32.
37. Meyer, M.W., Lupoi, J.S., Smith, E.A. (2011) 1064 nm dispersive multichannel Raman spectroscopy for the analysis of plant lignin. Anal. Chim. Acta 706:164-170.
38. Morikawa, Y., Yoshinaga, A., Kamitakahara, H., Wada, M., Takabe, K. (2010) Cellular distribution of coniferin in differentiating xylem of Chamaecyparis obtusa as revealed by Raman microscopy. Holzforschung 64:61-67.
39. Nakatsubo, F., Sato, K., Higuchi, T. (1975) Synthesis of guaiacylglycerol-® -guaiacyl ether. Holzforschung 29:165-168.
40. Nuopponen, M. FT-IR and UV Raman Spectroscopic Studies on Thermal Modification of Scots Pine Wood and its Extractable Compounds. Dissertation, Helsinki University of Technology, Espoo, 2005.
41. Olmstead, J., Gray, D. (1997) Fluorescence spectroscopy of cellulose, lignin and mechanical pulps: A review. J. Pulp Pap. Sci. 23:J571-J581. (Pubitemid 127628315)
42. Pandey, K.K., Vuorinen, T. (2008) UV resonance Raman spectroscopic study of photodegradation of hardwood and softwood lignins by UV laser. Holzforschung 62:183-188. (Pubitemid 351207843)
43. Pelletier, M.J. Analytical applications of Raman spectroscopy. Oxford, UK: Wiley-Blackwell, 1999.
44. Pelletier, M. (2003) Quantitative analysis using Raman spectrometry. Appl. Spectrosc. 57:20A-42A.
45. Pew, J.C., Connors, W.J. (1969) New structures from the enzymic dehydrogenation of lignin model p -hydroxy-〈 -carbinols. J. Org. Chem. 34:580-584.
46. Radotic, K., Kalauzi, A., Djikanovic, D., Jeremic, M., Leblanc, R.M., Cerovic, Z.G. (2006) Component analysis of the fluorescence spectra of a lignin model compound. J. Photochem. Photobiol. B 83:1-10. (Pubitemid 43372636)
47. Rana, R., Müller, G., Naumann, A., Polle, A. (2008) FTIR spectroscopy in combination with principal component analysis or cluster analysis as a tool to distinguish beech (Fagus sylvatica L) trees grown at different sites. Holzforschung 62:530-538.
48. Saariaho, A-M., Hortling, B., Jä äskeläinen, A-S., Tamminen, T., Vuorinen, T. (2003a) Simultaneous quantification of residual lignin and hexenuronic acid from chemical pulps with UV resonance Raman spectroscopy and multivariate calibration. J. Pulp Pap. Sci. 29:363-370.
49. Saariaho, A-M., Jä äskeläinen, A-S., Nuopponen, M., Vuorinen, T. (2003b) Ultra violet resonance Raman spectroscopy in lignin analysis: Determination of characteristic vibrations of p -hydroxyphenyl, guaiacyl, and syringyl lignin structures. Appl. Spectrosc. 57:58-66.
50. Saariaho, A-M., Jä äskeläinen, A-S., Matousek, P., Towrie, M., Parker, A.W., Vuorinen, T. (2004) Resonance Raman spectroscopy of highly fluorescing lignin containing chemical pulps: Suppression of fluorescence with an optical Kerr gate. Holzforschung 58:82-90.
51. Saariaho, A-M., Argyropoulos, D.S., Jä äskeläinen, A-S., Vuorinen, T. (2005) Development of the partial least squares models for the interpretation of the UV resonance Raman spectra of lignin model compounds. Vibrat. Spectrosc. 37:111-121. (Pubitemid 40072591)
52. Saito, Y., Sato, M. (2012) Carbonaceous structural changes of wood induced by microwave irradiation. Holzforschung 66:85-92.
53. Schulz, H., Baranska, M. (2007) Identification and quantification of valuable plant substances by IR and Raman spectroscopy. Vibrat. Spectrosc. 43:13-25. (Pubitemid 44960690)
54. Sipilä, J., Syrj änen, K. (1995) Synthesis and 13 C NMR spectroscopic characterisation of six dimeric arylglycerol-® -aryl ether model compounds representative of syringyl and p -hydroxyphenyl structures in lignins. On the aldol reaction in ® -ether preparation. Holzforschung 49:325-331.
55. Skoog, D.A. Principles of Instrumental Analysis. Brooks/Cole, Belmont, CA, 2000.
56. Smith, E., Dent, G. Modern Raman Spectroscopy: A Practical Approach. Wiley, Chichester, 2005.
57. Solala, I., Volperts, A., Andersone, A., Dizhbite, T., Mironova-Ulmane, N., Vehniäinen, A., Pere, J., Vuorinen, T. (2012) Mechanoradical formation and its effects on birch kraft pulp during the preparation of nanofibrillated cellulose with Masuko refining. Holzforschung 66:477-483.
58. Tamminen, T., Liitiä, T., Ohra-aho, T., Hortling, B. (2004) Do we need to isolate pulp residual lignin for its structural characterization. In: Proceedings of the 8th European Workshop of Lignocellulosics and Pulp, Riga, August 22-25. pp. 37-40.
59. Yoon, B. H., Yasuda, S., Terashima, N., Okada, M. (1979) Chromophoric structures of alkali lignin, 1: Reaction products from vanillyl alcohol with alkali. J. Jpn. Wood Res. Soc./Mokuzai Gakkaishi 25:302-307.
60. Zakzeski, J., Bruijnincx, P.C.A., Jongerius, A.L., Weckhuysen, B.M. (2010) The catalytic valorization of lignin for the production of renewable chemicals. Chem. Rev. 110:3552-3599.
61. Zakzeski, J., Bruijnincx, P.C.A., Weckhuysen, B.M. (2011) In situ spectroscopic investigation of the cobalt-catalyzed oxidation of lignin model compounds in ionic liquids. Green Chem. 13:671-680.