Clustering of Pentacene and Functionalized Pentacene Ions in a Matrix-Assisted Laser Desorption/Ionization Orthogonal TOF Mass Spectrometer

A high-performance orthogonal time-of flight (TOF) mass spectrometer, in combination with the matrix assisted laser desorption/ionization (MALDI) source operating at elevated pressure (∼1 torr in N2), was used to perform MALDI-TOF analyses of pentacene and some of its derivatives with and without an added matrix. These molecules are among the most interesting semiconductor materials for organic thin film transistor applications (OTFT). The observation of ion-molecule reactions between “cold” analyte ions and neutral analyte molecules in the gas phase has provided some insight into the mechanism of pentacene cluster formation and its functionalized derivatives. Furthermore, some of the matrices employed to assist the desorption/ionization process of these compounds were observed to influence the outcome via ion-molecule reactions of analyte ions and matrix molecules in the gas phase. The stability and reactivity of the compounds and their clusters in the MALDI plume during gas-phase expansion were evaluated; possible structures of the resulting clusters are discussed. The MALDI-TOF technique was also helpful in distinguishing between two isomeric forms of bis-[(triisopropylsilyl)-ethynyl]-pentacene.