Molecular assemblies on surfaces: towards physical and electronic decoupling of organic molecules

• Sabine Maier and
• Meike Stöhr

Beilstein J. Nanotechnol. 2021, 12, 950–956, doi:10.3762/bjnano.12.71

• from the substrates [73]. Suitable functionalization of molecules is another concept to vary their adsorption strength on metal substrates. For instance, partial fluorination of pentacene molecules decreased the adsorption strength on strongly interacting substrates such as Cu [74] but did not result

• in notable effects on Ag(111) [75]. Although this decoupling concept is only practical on Cu, the fluorination significantly changed the molecular multilayer growth on Ag(111) and led to a physical decoupling with a nearly bulk crystalline structure for the fluorinated pentacene. Two articles within

Controlling the electronic and physical coupling on dielectric thin films

• Philipp Hurdax,
• Michael Hollerer,
• Larissa Egger,
• Georg Koller,
• Xiaosheng Yang,
• Anja Haags,
• Serguei Soubatch,
• Frank Stefan Tautz,
• Mathias Richter,
• Alexander Gottwald,
• Peter Puschnig,
• Martin Sterrer and
• Michael G. Ramsey

Beilstein J. Nanotechnol. 2020, 11, 1492–1503, doi:10.3762/bjnano.11.132

• : decoupling; integer charge transfer; organic films; para-sexiphenyl; thin dielectric film; Introduction Since the first scanning tunneling microscope (STM) imaging of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of pentacene (5A) on NaCl/Cu(111) was

• /σ) in Figure 6b, according to: In order to determine the charge density, the knowledge of the density of charged molecules in the monolayer is required. In the case of pentacene, this could be reliably measured with STM, as 5A monolayers with all molecules charged could be produced. The LEED image

• transfer to 6P molecules. The simple relationship observed between the number of charged molecules and the work function change on the molecular adsorption proves that the charge transfer is governed by simple electrostatics. This confirms the conclusions drawn from a recent study with pentacene [20] and

Self-assembly and spectroscopic fingerprints of photoactive pyrenyl tectons on hBN/Cu(111)

• Domenik M. Zimmermann,
• Knud Seufert,
• Luka Ðorđević,
• Tobias Hoh,
• Sushobhan Joshi,
• Tomas Marangoni,
• Davide Bonifazi and
• Willi Auwärter

Beilstein J. Nanotechnol. 2020, 11, 1470–1483, doi:10.3762/bjnano.11.130

• (see Figure 6). Dissimilar responses of distinct MOs to work function variations were previously discussed, e.g., for pentacene on dielectric decoupling layers [23]. The assignment of the dI/dV signature to the MOs was corroborated by resolving the submolecular features in high-resolution STM images at

Impact of fluorination on interface energetics and growth of pentacene on Ag(111)

• Qi Wang,
• Meng-Ting Chen,
• Antoni Franco-Cañellas,
• Bin Shen,
• Thomas Geiger,
• Holger F. Bettinger,
• Frank Schreiber,
• Ingo Salzmann,
• Alexander Gerlach and
• Steffen Duhm

Beilstein J. Nanotechnol. 2020, 11, 1361–1370, doi:10.3762/bjnano.11.120

• . The F4PEN monolayer was essentially lying on Ag(111), and multilayers adopted π-stacking. Our study shed light not only on the F4PEN–Ag(111) interface but also on the fundamental adsorption behavior of fluorinated pentacene derivatives on metals in the context of interface energetics and growth mode

• ][21], which in turn affects the IEs. Overall, predicting the impact of fluorination on the energetics at organic–metal interfaces still remains a challenge. In this context, pentacene (PEN) and perfluorinated pentacene (PFP) are frequently-studied model compounds [9][18][22][23][24][25][26][27][28][29

• intramolecular interactions [18]. Overall, the influence of perfluorination on the multilayer growth and on the interfacial coupling of pentacene on clean metal surfaces is understood to a large extent. However, the impact of partial fluorination is less well studied, and thus we explored thin films of partially

Atomic defect classification of the H–Si(100) surface through multi-mode scanning probe microscopy

• Jeremiah Croshaw,
• Thomas Dienel,
• Taleana Huff and
• Robert Wolkow

Beilstein J. Nanotechnol. 2020, 11, 1346–1360, doi:10.3762/bjnano.11.119

• -functionalized AFM tips to image the molecular structure of pentacene [28]. Other functionalisations of AFM tips have been explored including Cu–O tips [29][30] and Xe tips [31][32]. The use of H2 [33][34] and D2 [35] provided the first successful demonstration of the enhanced imaging contrast by scanning

Hybridization vs decoupling: influence of an h-BN interlayer on the physical properties of a lander-type molecule on Ni(111)

• Maximilian Schaal,
• Takumi Aihara,
• Marco Gruenewald,
• Felix Otto,
• Jari Domke,
• Roman Forker,
• Hiroyuki Yoshida and
• Torsten Fritz

Beilstein J. Nanotechnol. 2020, 11, 1168–1177, doi:10.3762/bjnano.11.101

• DBP with Ni(111), presumably via the localized d bands, causes a drastic decrease of the mobility of the molecules hindering the highly ordered assembly of the molecules due to a hit-and-stick adsorption. Such a behavior was also observed for one monolayer of pentacene on Ni(111) [30]. In contrast

Templating effect of single-layer graphene supported by an insulating substrate on the molecular orientation of lead phthalocyanine

• K. Priya Madhuri,
• Abhay A. Sagade,
• Pralay K. Santra and
• Neena S. John

Beilstein J. Nanotechnol. 2020, 11, 814–820, doi:10.3762/bjnano.11.66

• and CuI. A FDTS layer induces the edge-on arrangement regardless of the crystal phase, while a CuI interlayer induces the formation of triclinic PbPc moieties stacked face-on to the substrate yielding enhanced NIR absorption [6]. Organic molecules such as pentacene, fullerene and sexithiophene have

• molecules such as FePc, CoPc, CuPc and ZnPc, which form layers in a face-on configuration [16][17][18][19]. A combination of brilliant synchrotron radiation and a highly sensitive 2D X-ray detector are employed to establish the structure and orientation of organic molecules such as MPcs, pentacene and P3HT

• -on configuration are still observed. In the case of CVD graphene transferred on to substrates by the polymer method, it has been reported that the presence of polymer residues can cause edge-on orientation for pentacene on graphene [11]. However, in this work, effort has been taken to remove any

A novel dry-blending method to reduce the coefficient of thermal expansion of polymer templates for OTFT electrodes

• Xiangdong Ye,
• Bo Tian,
• Yuxuan Guo,
• Fan Fan and
• Anjiang Cai

Beilstein J. Nanotechnol. 2020, 11, 671–677, doi:10.3762/bjnano.11.53

• silver target of 60 × 5 mm in size and purity of 99.99% as the OTFT electrode material was purchased from ZHNOGNUO New Material Co., Ltd., (Beijing, China). Pentacene as the semiconductor layer was used as purchased from Sigma-Aldrich and dissolved to a concentration of 5% in 1,2-dichlorobenzene

Mobility of charge carriers in self-assembled monolayers

• Zhihua Fu,
• Tatjana Ladnorg,
• Hartmut Gliemann,
• Alexander Welle,
• Asif Bashir,
• Michael Rohwerder,
• Qiang Zhang,
• Björn Schüpbach,
• Andreas Terfort and
• Christof Wöll

Beilstein J. Nanotechnol. 2019, 10, 2449–2458, doi:10.3762/bjnano.10.235

• performance of field effect transistor devices using pentacene as organic semiconductor [33]. In that work, the increase in performance was attributed to the reduced sheet resistance for charge transport in the anthracenethiol monolayer supporting the pentacene multilayer. In order to study the I–V

Ion mobility and material transport on KBr in air as a function of the relative humidity

• Dominik J. Kirpal,
• Korbinian Pürckhauer,
• Alfred J. Weymouth and
• Franz J. Giessibl

Beilstein J. Nanotechnol. 2019, 10, 2084–2093, doi:10.3762/bjnano.10.203

• as the imaging of single pentacene molecules by Gross et al. [12], intramolecular resolution of PTCDA at room temperature by Huber et al. [13], as well as the capability to perform non-destructive measurements on sensitive biological samples in air and in a liquid [14]. Moreover, it has been shown

Review of advanced sensor devices employing nanoarchitectonics concepts

• Katsuhiko Ariga,
• Tatsuyuki Makita,
• Masato Ito,
• Taizo Mori,
• Shun Watanabe and
• Jun Takeya

Beilstein J. Nanotechnol. 2019, 10, 2014–2030, doi:10.3762/bjnano.10.198

• sensing of general external environments such as pH, humidity, pressure, and magnetic field is undoubtedly important. Spanu et al. reported sensitive pH sensors based on organic charge-modulated field-effect transistor structures with 6,13-bis(triisopropylsilylethynyl)pentacene [95]. The fabricated

Pure and mixed ordered monolayers of tetracyano-2,6-naphthoquinodimethane and hexathiapentacene on the Ag(100) surface

• Robert Harbers,
• Timo Heepenstrick,
• Dmitrii F. Perepichka and
• Moritz Sokolowski

Beilstein J. Nanotechnol. 2019, 10, 1188–1199, doi:10.3762/bjnano.10.118

• have a “great potential for use in next-generation textile and wearable electronics” [22]. HTPEN was investigated as a material for organic solar cells [23], for which purpose it was combined with lead(II) phthalocyanine and pentacene. These heterostructures exhibit a greater range of photosensitivity

• than pure pentacene films. As the acceptor-type molecule we used TNAP, which is a π-extended analogue of TCNQ (Figure 1d), from which it is synthesized [24]. TCNQ and TNAP are both known to act as electron acceptors in organic CT salts [17][25]. Umbach et al. [16] found mixed layers of TNAP in

• for 60 min prior to the deposition of the molecules. HTPEN was synthesized as green microcrystalline substance by reacting pentacene with an excess of elemental sulfur in 1,2,4-trichlorobenzene solution at 210 °C, according to the published procedure [31]. The analytical data was identical to that

Nitrous oxide as an effective AFM tip functionalization: a comparative study

• Taras Chutora,
• Bruno de la Torre,
• Pingo Mutombo,
• Jack Hellerstedt,
• Jaromír Kopeček,
• Pavel Jelínek and
• Martin Švec

Beilstein J. Nanotechnol. 2019, 10, 315–321, doi:10.3762/bjnano.10.30

• . Functionalization of a metallic tip apex with a single carbon monoxide molecule (CO) was the key to achieve submolecular resolution for the first time, on a pentacene molecule [1]. This milestone initiated a vigorous development of the technique that now serves a variety of purposes. For example, it can identify

Artifacts in time-resolved Kelvin probe force microscopy

• Sascha Sadewasser,
• Nicoleta Nicoara and
• Santiago D. Solares

Beilstein J. Nanotechnol. 2018, 9, 1272–1281, doi:10.3762/bjnano.9.119

• approach (pp-KPFM) was used to measure the charge-carrier dynamics with a time resolution of 2 μs in pentacene-based OFETs [28][29]. Similarly, light-based pp-KPFM was used to measure a charge carrier lifetime in low-temperature grown GaAs of ≈1 ps, currently the best time-resolution that has been

Towards molecular spintronics

• Georgeta Salvan and
• Dietrich R. T. Zahn

Beilstein J. Nanotechnol. 2017, 8, 2464–2466, doi:10.3762/bjnano.8.245

• considered molecules spans from heterotrinuclear bis(oxamato)-type and bis(oxamidato)-type complexes [1][2][3], to exchange-coupled dinickel complexes [4], metallo-phthalocyanines [5][6][7], metallo-porphyrins [8][9] and charge-transfer complexes [10][11], to metal-free molecules like pentacene-derivatives

Parylene C as a versatile dielectric material for organic field-effect transistors

• Tomasz Marszalek,
• Maciej Gazicki-Lipman and
• Jacek Ulanski

Beilstein J. Nanotechnol. 2017, 8, 1532–1545, doi:10.3762/bjnano.8.155

• the first few semiconductor layers as well as on the size of its crystal grains is a critical factor in high-performance OFET devices. The effect of Parylene C roughness on charge transport has been studied in detail by an observation of submonolayer percolation of a pentacene film during its

• accumulation of metastable positive charges at the dielectric/semiconductor interface during the bias stressing. A similar behavior of bidirectional Vth shift was also observed in pentacene OFETs on silicon dioxide substrates modified by polydimethylsiloxane and it was assigned to either hole or electron

• unchanged impedance of the microelectrodes protected by Parylene C layers has been recorded for over four months [66]. As another positive result, no destructive influence of the encapsulation material was observed when Parylene C had been employed to protect a pentacene OFET device, where no remarkable

Light-induced magnetoresistance in solution-processed planar hybrid devices measured under ambient conditions

• Sreetama Banerjee,
• Daniel Bülz,
• Danny Reuter,
• Karla Hiller,
• Dietrich R. T. Zahn and
• Georgeta Salvan

Beilstein J. Nanotechnol. 2017, 8, 1502–1507, doi:10.3762/bjnano.8.150

• report light-induced negative organic magnetoresistance (OMAR) measured in ambient atmosphere in solution-processed 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene) planar hybrid devices with two different device architectures. Hybrid electronic devices with trench-isolated electrodes (HED

• higher for the HED-TIE devices because of the much smaller channel length of these devices compared to the OFETs. We attribute the observed light-induced negative magnetoresistance in TIPS-pentacene to the presence of electron–hole pairs under illumination as the magnetoresistive effect scales with the

• -pentacene film. Keywords: HED-TIEs; hybrid electronic devices; organic field-effect transistors (OFETs); organic magnetoresistance; planar hybrid devices; TIPS-pentacene; Findings The field of molecular spintronics has received lot of research interest in the last years because of the possibility of

Adsorption and electronic properties of pentacene on thin dielectric decoupling layers

• Sebastian Koslowski,
• Daniel Rosenblatt,
• Alexander Kabakchiev,
• Klaus Kuhnke,
• Klaus Kern and
• Uta Schlickum

Beilstein J. Nanotechnol. 2017, 8, 1388–1395, doi:10.3762/bjnano.8.140

• electronic properties of pentacene deposited onto h-BN/Rh(111) and compare them with those of pentacene deposited onto KCl on various metal surfaces. When deposited onto KCl, the HOMO and LUMO energies of the pentacene molecules scale with the work functions of the combined KCl/metal surface. The magnitude

• individual molecules on thin electronically decoupling layers. Depositing pentacene onto h-BN/Rh(111) results in significantly different adsorption characteristics, due to the topographic corrugation of the surface as well as the lateral electric fields it presents. These properties are reflected in the

• divergence from the aforementioned trend for the orbital energies of pentacene deposited onto h-BN/Rh(111), as well as in the different adsorption geometry. Thus, the highly desirable capacity of h-BN to trap molecules comes at the price of enhanced metal–molecule interaction, which decreases the HOMO–LUMO

Core-level spectra and molecular deformation in adsorption: V-shaped pentacene on Al(001)

• Anu Baby,
• He Lin,
• Gian Paolo Brivio,
• Luca Floreano and
• Guido Fratesi

Beilstein J. Nanotechnol. 2015, 6, 2242–2251, doi:10.3762/bjnano.6.230

• Studi di Milano, Via Celoria 16, I-20133 Milano, Italy 10.3762/bjnano.6.230 Abstract By first-principle simulations we study the effects of molecular deformation on the electronic and spectroscopic properties as it occurs for pentacene adsorbed on the most stable site of Al(001). The rationale for the

• splitting of the sigma resonances measured along the two in-plane molecular axes. Keywords: aluminum; density functional theory (DFT); near-edge X-ray absorption fine structure (NEXAFS); pentacene; X-ray photoelectron spectroscopy (XPS); Introduction Pentacene has been studied extensively as it is a

• potential candidate in the field of organic electronic devices [1][2][3][4][5]. It acts as a p-type organic semiconductor in its intrinsic state with high hole mobility and exhibits a very high melting point [6]. The pentacene–Al junction is known to exhibit a Schottky barrier and, hence, finds numerous

Non-covalent and reversible functionalization of carbon nanotubes

• Antonello Di Crescenzo,
• Valeria Ettorre and
• Antonella Fontana

Beilstein J. Nanotechnol. 2014, 5, 1675–1690, doi:10.3762/bjnano.5.178

• amount of pyrene in THF indicated that the adsorption process is reversible. Instead tetracene and pentacene were investigated by X-ray photoelectron spectroscopy [45]. The more than six times greater adsorption of tetracene with respect to that of phenanthrene was imputed to the nanoscale curvature of

Organic and inorganic–organic thin film structures by molecular layer deposition: A review

• Pia Sundberg and
• Maarit Karppinen

Beilstein J. Nanotechnol. 2014, 5, 1104–1136, doi:10.3762/bjnano.5.123

Influence of the adsorption geometry of PTCDA on Ag(111) on the tip–molecule forces in non-contact atomic force microscopy

• Gernot Langewisch,
• Jens Falter,
• André Schirmeisen and
• Harald Fuchs

Beilstein J. Nanotechnol. 2014, 5, 98–104, doi:10.3762/bjnano.5.9

• in Figure 2, in which the five carbon rings of the perylene core are visible, is provided by Gross and Moll et al. [8][16]. As was found for the first time for pentacene molecules and later also for PTCDA adsorbed on Cu(111), the atomic contrast revealing the carbon rings of organic molecules can be

Probing three-dimensional surface force fields with atomic resolution: Measurement strategies, limitations, and artifact reduction

• Mehmet Z. Baykara,
• Omur E. Dagdeviren,
• Todd C. Schwendemann,
• Harry Mönig,
• Eric I. Altman and
• Udo D. Schwarz

Beilstein J. Nanotechnol. 2012, 3, 637–650, doi:10.3762/bjnano.3.73

• sample surface. Force fields have now been recorded on NiO(001) [10][12][13], MgO/Ag(001) [14], NaCl(001) [15][16], Si(111)-(7×7) [17][18][19], HOPG [20][21], KBr(001) [9][22][23], Cu(111) [24], and CaCO3() [25] surfaces, as well as single molecules of PTCDA [26][27], pentacene [28], CO [29], C60 [30

Graphite, graphene on SiC, and graphene nanoribbons: Calculated images with a numerical FM-AFM

• Fabien Castanié,
• Laurent Nony,
• Sébastien Gauthier and
• Xavier Bouju

Beilstein J. Nanotechnol. 2012, 3, 301–311, doi:10.3762/bjnano.3.34

• various molecular systems [3][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59]. Recently, impressive results were shown with single pentacene C22H14 and C16H10N2O2 molecules adsorbed on a thin NaCl film deposited on a Cu(111) surface [52][53]. These breakthroughs were possible with a

An NC-AFM and KPFM study of the adsorption of a triphenylene derivative on KBr(001)

• Antoine Hinaut,
• Adeline Pujol,
• Florian Chaumeton,
• David Martrou,
• André Gourdon and
• Sébastien Gauthier

Beilstein J. Nanotechnol. 2012, 3, 221–229, doi:10.3762/bjnano.3.25

• room for progress as shown by the impressive submolecular resolution that has been demonstrated in recent works on the adsorption of pentacene [14] or decastarphene [15] molecules on Cu(111) and on a NaCl(001) bilayer on Cu(111). During the same period, Kelvin probe force microscopy (KPFM) has been