Drawing a different picture with pencil lead as matrix-assisted laser desorption/ionization matrix for fullerene derivatives

Abstract

Inspired by reports on the use of pencil lead as a matrix-assisted laser desorption/ionization matrix, paving the way towards matrix-free matrix-assisted laser desorption/ionization, the present investigation evaluates its usage with organic fullerene derivatives. Currently, this class of compounds is best analysed using the electron transfer matrix trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene] malononitrile (DCTB), which was employed as the standard here. The suitability of pencil lead was additionally compared to direct (i.e. no matrix) laser desorption/ionization-mass spectrometry. The use of (DCTB) was identified as the by far gentler method, producing spectra with abundant molecular ion signals and much reduced fragmentation. Analytically, pencil lead was found to be ineffective as a matrix, however, appears to be an extremely easy and inexpensive method for producing sodium and potassium adducts.

Keywords

Matrix-assisted laser desorption/ionization pencil lead (DCTB)sodium and potassium adducts matrix fullerene derivatives

Get full access to this article

View all access options for this article.

References

Guinan

Kirkbride

Pigou

et al.

Surface-assisted laser desorption ionization mass spectrometry techniques for application in forensics. Mass Spectrom Rev 2015; 34: 627.

Rainer

Qureshi

Bonn

. Matrix-free and material-enhanced laser desorption/ionization mass spectrometry for the analysis of low molecular weight compounds. Anal Bioanal Chem 2011; 400: 2281.

Kuzema

. Small-molecule analysis by surface-assisted laser desorption/ionization mass spectrometry. J Anal Chem 2011; 66: 1227.

Peterson

. Matrix-free methods for laser desorption/ionization mass spectrometry. Mass Spectrom Rev 2007; 26: 19.

Najam-ul-Haq

Rainer

Szabo

et al.

Role of carbon nano-materials in the analysis of biological materials by laser desorption/ionization-mass spectrometry. J Biochem Biophys Meth 2007; 70: 319.

Coffinier

Boukherroub

Szunerits

Carbon-based nanostructures for matrix-free mass spectrometry. In: Yang

Jiang

Pang

(eds). Carbon nanoparticles and nanostructures, Cham: Springer International Publishing, 2016, pp. 331.

Lewis

Shen

Finn

et al.

Desorption/ionization on silicon (DIOS) mass spectrometry: background and applications. Int J Mass Spectrom 2003; 226: 107.

Black

Poile

Langley

et al.

The use of pencil lead as a matrix and calibrant for matrix-assisted laser desorption/ionisation. Rapid Commun Mass Spectrom 2006; 20: 1053.

Langley

Herniman

Townell

. 2B or not 2B, that is the question: further investigations into the use of pencil as a matrix for matrix-assisted laser desorption/ionisation. Rapid Commun Mass Spectrom 2007; 21: 180.

10.

Dale

Knochenmuss

Zenobi

. Graphite/liquid mixed matrices for laser desorption/ionization mass spectrometry. Anal Chem 1996; 68: 3321.

11.

Sunner

Dratz

Chen

. Graphite surface-assisted laser desorption/ionization time-of-flight mass spectrometry of peptides and proteines from liquid solutions. Anal Chem 1995; 67: 4335.

12.

Hopwood

Michalak

Alderdice

et al.

C60-assisted laser desorption/ionization mass spectrometry in the analysis of phosphotungstic acid. Rapid Commun Mass Spectrom 1994; 8: 881.

13.

Shiea

huang

Teng

et al.

The use of water-soluble fullerene derivative as precipitating reagent and matrix-assisted laser desorption/ionization matrix to selectively detect charged species in aqueous solutions. Anal Chem 2003; 75: 3587.

14.

Zou

et al.

Carbon nanotubes as assisted matrix for laser desorption/ionization time-of-flight mass spectrometry. Anal Chem 2003; 75: 6191.

15.

Traldi

Calandra

Crotti

et al.

Matrix-assisted laser desorption/ionization, nanostructure-assisted laser desorption/ionization and carbon nanohorns in the dectection of antineoplastic drugs. 1. The case of irinotecan, sunitinib and 6-alpha-hydroxy paclitaxel. Eur J Mass Spectrom 2014; 20: 445.

16.

Dong

Cheng

et al.

Graphene as a novel matrix for the analysis of small molecules by MALDI-TOF MS. Anal Chem 2010; 82: 6208.

17.

Berger-Nicoletti

Wurm

Kilbinger

AFM

et al.

Pencil lead as a matrix for MALDI-ToF mass spectrometry of sensitive functional polymers. Macromolecules 2007; 40: 746.

18.

Kim

Han

Kim

et al.

Detection of long alkyl esters of succinic and maleic acid using TLC-MALDI MS. Bull Kor Chem Soc 2011; 32: 915.

19.

Shenar

Cantel

Martinez

et al.

Comparison of inert supports in laser desorption/ionization mass spectrometry of peptides: pencil lead, porous silica gel, DIOS-chip and NALDI™ target. Rapid Commun Mass Spectrom 2009; 23: 2371.

20.

Warren

Conway

Arthur

et al.

Investigation of colloidal graphite as a matrix for matrix-assisted laser desorption/ionisation mass spectrometry of low molecular weight analytes. J Mass Spectrom 2016; 51: 491.

21.

Hirsch

Lamparth

Karfunkel

. Fullerene chemistry in three dimensions: isolation of seven regioisomeric bisadducts and chiral trisadducts of C₆₀ and di(ethoxycarbonyl)methylene. Angew Chem Int Ed Engl 1994; 33: 437.

22.

Hirsch

Lamparth

Grösser

et al.

Regiochemistry of multiple additions to the fullerene core: synthesis of a Th-symmetric hexacisadduct of C60 with bis(ethoxycarbonyl)methylene. J Am Chem Soc 1994; 116: 9385.

23.

Hirsch

Brettreich

. Fullerenes: Chemistry and reactions, Weinheim: Wiley-VCH Verlag, 2004.

24.

Beck

Weis

Hirsch

et al.

Laser desorption mass spectrometry of fullerene derivatives: laser-induced fragmentation and coalescence reactions. J Phys Chem 1994; 98: 9683.

25.

Brown

Clipston

Simjee

et al.

Matrix-assisted laser desorption/ionization of amphiphilic fullerene derivatives. Int J Mass Spectrom 2001; 210/211: 249.

26.

Streletskii

Ioffe

Kotsiris

et al.

In-plume thermodynamics of the MALDI generation of fluorofullerene anions. J Phys Chem A 2005; 109: 714.

27.

Vasil'ev

Khvostenko

Streletskii

et al.

Electron transfer reactivity in matrix-assisted laser desorption/ionization (MALDI): ionization energy, electron affinity and performance of the DCTB matrix within the thermochemical framework. J Phys Chem A 2006; 110: 5967.

28.

Vasil'ev

Kotsiris

Bashkin

et al.

Bulk Produktion of a strong covalently linked (C₆₀H_x)₂ dimer. J Phys Chem B 2005; 109: 11875.

29.

Fati

Leeman

Vasil'ev

et al.

Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization. J Am Soc Mass Spectrom 2002; 13: 1448.

30.

Fati

Vasil'ev

Wachter

et al.

MALDI mass spectrometric determination of molecular site-specific charge localisation, and laser-induced coalescence reactivity of fullerenodendrimers. Int J Mass Spectrom 2003; 229: 3.

31.

Nye

Tzirakis

Orfanopoulos

et al.

C₆₀H₂: Recover and decline – an investigation by MALDI mass spectrometry. Chem Phys Lett 2010; 499: 209.

32.

Kotsiris

Vasil'ev

Streletskii

et al.

Application and evaluation of solvent-free matrix-assisted laser desorption/ionization mass spectrometry for the analysis of derivatisezed fullerenes. Eur J Mass Spectrom 2006; 12: 397.