Bis(triisopropylsilylethynyl)pentacene/Au(111) interface: Coupling, molecular orientation, and thermal stability

Handle URI:
http://hdl.handle.net/10754/575617
Title:
Bis(triisopropylsilylethynyl)pentacene/Au(111) interface: Coupling, molecular orientation, and thermal stability
Authors:
Gnoli, Andrea; Üstünel, Hande; Toffoli, Daniele; Yu, Liyang; Catone, D.; Turchini, Stefano; Lizzit, Silvano; Stingelin, Natalie; Larciprête, Rosanna
Abstract:
The assembly and the orientation of functionalized pentacene at the interface with inorganics strongly influence both the electric contact and the charge transport in organic electronic devices. In this study electronic spectroscopies and theoretical modeling are combined to investigate the properties of the bis(triisopropylsilylethynyl)pentacene (TIPS-Pc)/Au(111) interface as a function of the molecular coverage to compare the molecular state in the gas phase and in the adsorbed phase and to determine the thermal stability of TIPS-Pc in contact with gold. Our results show that in the free molecule only the acene atoms directly bonded to the ligands are affected by the functionalization. Adsorption on Au(111) leads to a weak coupling which causes only modest binding energy shifts in the TIPS-Pc and substrate core level spectra. In the first monolayer the acene plane form an angle of 33 ± 2° with the Au(111) surface at variance with the vertical geometry reported for thicker solution-processed or evaporated films, whereas the presence of configurational disorder was observed in the multilayer. The thermal annealing of the TIPS-Pc/Au(111) interface reveals the ligand desorption at ∼470 K, which leaves the backbone of the decomposed molecule flat-lying on the metal surface as in the case of the unmodified pentacene. The weak interaction with the metal substrate causes the molecular dissociation to occur 60 K below the thermal decomposition taking place in thick drop-cast films.
KAUST Department:
Materials Science and Engineering Program
Publisher:
American Chemical Society (ACS)
Journal:
The Journal of Physical Chemistry C
Issue Date:
2-Oct-2014
DOI:
10.1021/jp504401v
Type:
Article
ISSN:
19327447
Sponsors:
The authors dedicate this paper to the memory of Gianluca Latini, who had initiated this project with passion and enthusiasm. The support of the SuperESCA and CiPo beamline staffs of Elettra is deeply acknowledged. The research leading to these results has received funding from the European Community's Seventh Framework Programme (FP7/2007-2013) under grant agreement no. 226716.
Appears in Collections:
Articles; Materials Science and Engineering Program

Full metadata record

DC FieldValue Language
dc.contributor.authorGnoli, Andreaen
dc.contributor.authorÜstünel, Handeen
dc.contributor.authorToffoli, Danieleen
dc.contributor.authorYu, Liyangen
dc.contributor.authorCatone, D.en
dc.contributor.authorTurchini, Stefanoen
dc.contributor.authorLizzit, Silvanoen
dc.contributor.authorStingelin, Natalieen
dc.contributor.authorLarciprête, Rosannaen
dc.date.accessioned2015-08-24T08:34:18Zen
dc.date.available2015-08-24T08:34:18Zen
dc.date.issued2014-10-02en
dc.identifier.issn19327447en
dc.identifier.doi10.1021/jp504401ven
dc.identifier.urihttp://hdl.handle.net/10754/575617en
dc.description.abstractThe assembly and the orientation of functionalized pentacene at the interface with inorganics strongly influence both the electric contact and the charge transport in organic electronic devices. In this study electronic spectroscopies and theoretical modeling are combined to investigate the properties of the bis(triisopropylsilylethynyl)pentacene (TIPS-Pc)/Au(111) interface as a function of the molecular coverage to compare the molecular state in the gas phase and in the adsorbed phase and to determine the thermal stability of TIPS-Pc in contact with gold. Our results show that in the free molecule only the acene atoms directly bonded to the ligands are affected by the functionalization. Adsorption on Au(111) leads to a weak coupling which causes only modest binding energy shifts in the TIPS-Pc and substrate core level spectra. In the first monolayer the acene plane form an angle of 33 ± 2° with the Au(111) surface at variance with the vertical geometry reported for thicker solution-processed or evaporated films, whereas the presence of configurational disorder was observed in the multilayer. The thermal annealing of the TIPS-Pc/Au(111) interface reveals the ligand desorption at ∼470 K, which leaves the backbone of the decomposed molecule flat-lying on the metal surface as in the case of the unmodified pentacene. The weak interaction with the metal substrate causes the molecular dissociation to occur 60 K below the thermal decomposition taking place in thick drop-cast films.en
dc.description.sponsorshipThe authors dedicate this paper to the memory of Gianluca Latini, who had initiated this project with passion and enthusiasm. The support of the SuperESCA and CiPo beamline staffs of Elettra is deeply acknowledged. The research leading to these results has received funding from the European Community's Seventh Framework Programme (FP7/2007-2013) under grant agreement no. 226716.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleBis(triisopropylsilylethynyl)pentacene/Au(111) interface: Coupling, molecular orientation, and thermal stabilityen
dc.typeArticleen
dc.contributor.departmentMaterials Science and Engineering Programen
dc.identifier.journalThe Journal of Physical Chemistry Cen
dc.contributor.institutionCNR-ISC Istituto Dei Sistemi Complessi, Via Fosso del Cavaliere 100Rome, Italyen
dc.contributor.institutionDepartment of Physics, Middle East Technical UniversityAnkara, Turkeyen
dc.contributor.institutionDepartment of Chemistry, Middle East Technical UniversityAnkara, Turkeyen
dc.contributor.institutionCNR-ISM Istituto di Struttura della Materia, Via Fosso del Cavaliere 100Rome, Italyen
dc.contributor.institutionElettra-Sincrotrone Trieste S.C.p.A., AREA Science Park, S.S. 14 km 163.5Trieste, Italyen
dc.contributor.institutionDepartment of Materials, Imperial College LondonLondon, United Kingdomen
kaust.authorYu, Liyangen
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