Ordering of Zn-centered porphyrin and phthalocyanine on TiO₂(011): STM studies

• Piotr Olszowski,
• Lukasz Zajac,
• Szymon Godlewski,
• Bartosz Such,
• Rémy Pawlak,
• Antoine Hinaut,
• Res Jöhr,
• Thilo Glatzel,
• Ernst Meyer and
• Marek Szymonski

Beilstein J. Nanotechnol. 2017, 8, 99–107, doi:10.3762/bjnano.8.11

• conditions. Keywords: dye-sensitized solar cells; molecular nanostructures; phthalocyanines; porphyrins; rutile surfaces; STM imaging; Introduction There is an increasing interest in optoelectronic applications of organic molecular heterostructures which utilize inorganic substrates, such as titanium

• role. In general, they depend not only on the characteristics of the individual building blocks, but are also sensitive to the organic–inorganic interface and the molecule orientation [4][5]. In this context, metal containing phthalocyanines and porphyrins are very often used for microscopic studies

• device functionality. It was reported that a mixture of porphyrins and phthalocyanine has a profound impact on the photovoltaic parameters of dye-sensitized solar cells [9][10]. Therefore, the microscopic investigation on such systems is crucial. One of the most popular nonmetal substrates used for

Scanning probe microscopy studies on the adsorption of selected molecular dyes on titania

• Jakub S. Prauzner-Bechcicki,
• Lukasz Zajac,
• Piotr Olszowski,
• Res Jöhr,
• Antoine Hinaut,
• Thilo Glatzel,
• Bartosz Such,
• Ernst Meyer and
• Marek Szymonski

Beilstein J. Nanotechnol. 2016, 7, 1642–1653, doi:10.3762/bjnano.7.156

• prototypical dye molecules, i.e., perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA), phtalocyanines and porphyrins. Two interesting heteromolecular systems comprising molecules that are aligned with the given review are discussed as well. Keywords: dye molecules; perylene-3,4,9,10-tetracarboxylic

• dianhydride (PTCDA); phtalocyanines; porphyrins; rutile; scanning probe microscopy; scanning tunneling microscopy (STM); titanium dioxide (TiO2); Introduction Today it comes as no surprise that photovoltaic devices can be made of materials other than silicon. Nanocrystalline materials accompanied by organic

• ), phthalocyanines (Pcs) and porphyrins (Figure 1). All of these molecules are dyes absorbing in the visible range, and all of them are used in photovoltaic applications [13][14][15][16][17][18][19][20][21]. They are also intensively studied using various surface sensitive methods. Surprisingly, however, for each

Filled and empty states of Zn-TPP films deposited on Fe(001)-p(1×1)O

• Gianlorenzo Bussetti,
• Alberto Calloni,
• Rossella Yivlialin,
• Andrea Picone,
• Federico Bottegoni and
• Marco Finazzi

Beilstein J. Nanotechnol. 2016, 7, 1527–1531, doi:10.3762/bjnano.7.146

• (typically 20 ML) porphyrin film is used for this purpose [10][11]. There, the substrate is almost completely covered by porphyrins. The spectra acquired on thick films can be considered representative of the electronic properties of a hypothetical isolated molecule, since molecule–molecule interactions are

• prototypical of the wide class of thin MO films. The ultrathin oxide layer is able to decouple the molecules from the buried iron substrate. The reduced molecule–substrate interaction allows preservation of the main electronic properties of the Zn-TPP porphyrins. This means that the HOMO and LUMO levels of the

Optical absorption signature of a self-assembled dye monolayer on graphene

• Tessnim Sghaier,
• Sylvain Le Liepvre,
• Céline Fiorini,
• Ludovic Douillard and
• Fabrice Charra

Beilstein J. Nanotechnol. 2016, 7, 862–868, doi:10.3762/bjnano.7.78

• porphyrins on h-BN [9]. However, the PTCDI molecule already present a rigid intrinsically planar covalent structure and substrate-induced planarization cannot explain the even larger shift observed here. The graphene has a much larger polarizability than h-BN. Hence, the strongly increased polarizability of

Hierarchical coassembly of DNA–triptycene hybrid molecular building blocks and zinc protoporphyrin IX

• Rina Kumari,
• Sumit Singh,
• Mohan Monisha,
• Sourav Bhowmick,
• Anindya Roy,
• Neeladri Das and
• Prolay Das

Beilstein J. Nanotechnol. 2016, 7, 697–707, doi:10.3762/bjnano.7.62

• polymeric networks [46][47]. In this study, we report the synthesis of the DNA–TPA scaffolds by covalent conjugation of 2,6,14-triptycenetripropiolic acid (TPA) with amine-modified 12-mer ssDNA and coassembly with zinc protoporphyrin IX(Zn PpIX) to form composite DNA nanostructures (Scheme 1). Porphyrins

• in the present study is two-fold. Firstly, in the interaction of Zn PpIX with DNA, the former is hypothesized to provide template for assembly formation [45]. Secondly, the generation of ROS through excitation of porphyrins is an established fact [48]. The covalent conjugation of TPA with ssDNA was

Rigid multipodal platforms for metal surfaces

• Michal Valášek,
• Marcin Lindner and
• Marcel Mayor

Beilstein J. Nanotechnol. 2016, 7, 374–405, doi:10.3762/bjnano.7.34

• tetraphenylmethane with three acetylsulfanylmethyl groups 36 (Figure 15) for surface attachment to examine the effects of spatial arrangement of the molecular structure on charge storage in SAMs [72]. The redox-active molecules include ferrocene, zinc porphyrins, magnesium phthalocyanine, and triple-decker

Conformational switching of ethano-bridged Cu,H₂-bis-porphyrin induced by aromatic amines

• Simona Bettini,
• Emanuela Maglie,
• Rosanna Pagano,
• Victor Borovkov,
• Yoshihisa Inoue,
• Ludovico Valli and
• Gabriele Giancane

Beilstein J. Nanotechnol. 2015, 6, 2154–2160, doi:10.3762/bjnano.6.221

• resonance; Introduction Various porphyrin derivatives, both free-base and metal complexes, have been widely employed as active molecules for detecting analytes in vapor as well as in liquid phase [1][2][3]. Porphyrins are endowed with good host material properties and the ability to form films [4

• ], allowing realization of thin film devices with variable physical and chemical properties upon complexation with guest molecules [5][6][7]. One of the most appealing classes of porphyrins is the bis-porphyrins, which can switch their conformational form as a result of the interaction with specific guest

• molecules, such as analytes [8]. For example, in the case of ethano-bridged bis-porphyrins, the structural change between the closed form (syn-form, Figure 1a) and the open form (anti-form, Figure 1b) can be easily detected by various spectroscopic methods. Previously it was shown that doubly metallated bis

Electrospray deposition of organic molecules on bulk insulator surfaces

• Antoine Hinaut,
• Rémy Pawlak,
• Ernst Meyer and
• Thilo Glatzel

Beilstein J. Nanotechnol. 2015, 6, 1927–1934, doi:10.3762/bjnano.6.195

• porphyrins To enable the analysis of single molecules, annealing of the sample should be avoided to restrict diffusion processes. Different parameters that could lead to a reduced amount of deposited molecules and charges can be tuned, like reducing deposition time or molecule concentration in the solution

• according to the synthetic protocols by D. Bonifazi et al. [39]. The inset shows a molecular scheme and the dimensions. b) Topography image after the UHV-ESI deposition of the porphyrins on KBr(001) for 5 min. Scan parameter: A = 2 nm, Δf = −25 Hz, U = −10 V. Topography image (400 × 400 nm2) of diporphyrins

Spectroscopic mapping and selective electronic tuning of molecular orbitals in phosphorescent organometallic complexes – a new strategy for OLED materials

• Pascal R. Ewen,
• Jan Sanning,
• Tobias Koch,
• Nikos L. Doltsinis,
• Cristian A. Strassert and
• Daniel Wegner

Beilstein J. Nanotechnol. 2014, 5, 2248–2258, doi:10.3762/bjnano.5.234

• the relevant frontier orbitals [11][12][13][14][15]. Several studies have performed STM and STS on organometallic compounds, mainly on porphyrins and phthalocyanines [16][17][18][19][20][21][22]. Considering this general success, it is surprising that phosphorescent complexes have barely been

Optical properties and electrical transport of thin films of terbium(III) bis(phthalocyanine) on cobalt

• Peter Robaschik,
• Pablo F. Siles,
• Daniel Bülz,
• Peter Richter,
• Manuel Monecke,
• Michael Fronk,
• Svetlana Klyatskaya,
• Daniel Grimm,
• Oliver G. Schmidt,
• Mario Ruben,
• Dietrich R. T. Zahn and
• Georgeta Salvan

Beilstein J. Nanotechnol. 2014, 5, 2070–2078, doi:10.3762/bjnano.5.215

• exhibit a higher hole mobility as compared to the porphyrins [25], which could lead to a higher current. When comparing the topographic characteristics of TbPc2 samples with 20 nm and 80 nm (see Figures 4 and 5), the variation with grain size would induce more grain boundaries for electron scattering in

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

• π-stacking as no solvophobic forces can participate in the interactions with the SWCNT walls. This functionalization leaves virtually intact the inherent properties of SWCNTs, as observed by several photophysical measurements. Porphyrins (see Table 1) demonstrated [48] to physically adsorb onto the

Donor–acceptor graphene-based hybrid materials facilitating photo-induced electron-transfer reactions

• Anastasios Stergiou,
• Georgia Pagona and
• Nikos Tagmatarchis

Beilstein J. Nanotechnol. 2014, 5, 1580–1589, doi:10.3762/bjnano.5.170

• obtaining donor–acceptor hybrid materials based on graphene to facilitate charge-transfer phenomena, which is reviewed here, concerns the incorporation of porphyrins and phthalocyanines onto graphene sheets. Through illustrative schemes, the preparation and most importantly the photophysical properties of

• materials composed of graphene and photoactive components, such as porphyrins and phthalocyanines, have been prepared and evaluated regarding photo-induced charge transfer phenomena [16][17][18]. Moreover, semiconducting quantum dots such as CdS [19][20][21][22], CdSe [23][24][25][26], CdTe [27][28], ZnO

• on graphene oxide or reduced graphene oxide The unique and notable features of porphyrins and phthalocyanines as light-harvesting antennas with high extinction coefficients and remarkable redox properties make them promising electron donors to be associated with graphene. The very first approach of

Nanostructure sensitization of transition metal oxides for visible-light photocatalysis

• Hongjun Chen and
• Lianzhou Wang

Beilstein J. Nanotechnol. 2014, 5, 696–710, doi:10.3762/bjnano.5.82

• as photosensitizers for transition metal oxides. Note that various organic dyes such as rhodamine B, porphyrins, and phthalocyanines have been employed as photosensitizers [11][12][13][14] and these dyes also play an important role in the photosensitization of dye-sensitized solar cells (DSSCs) [15

Fullerenes as adhesive layers for mechanical peeling of metallic, molecular and polymer thin films

• Maria B. Wieland,
• Anna G. Slater,
• Barry Mangham,
• Neil R. Champness and
• Peter H. Beton

Beilstein J. Nanotechnol. 2014, 5, 394–401, doi:10.3762/bjnano.5.46

• of this molecular adhesive layer provides a new route to transfer polymeric films from metal substrates to other surfaces as we demonstrate for an assembly of covalently-coupled porphyrins. Keywords: polymerisation; porphyrin; surface; thin film; transfer; Introduction The mechanical removal of

• apart irregularly. Due to the thermal stability of the covalent bonds linking neighbouring porphyrins, the residual C60 can be removed by annealing without removing the polymeric network (note that a similar annealing treatment applied to non-polymerised porphyrins results in complete removal of the

• monolayers; the peaks are observed at, within experimental error, the same wavelength as the monomer. These observations are consistent with previous studies of arrays of porphyrins coupled by phenyl groups [37]. The very weak coupling of neighbouring porphyrins has been attributed to the rotation of the

Morphological characterization of fullerene–androsterone conjugates

• Alberto Ruiz,
• Margarita Suárez,
• Nazario Martin,
• Fernando Albericio and
• Hortensia Rodríguez

Beilstein J. Nanotechnol. 2014, 5, 374–379, doi:10.3762/bjnano.5.43

• suitably functionalized fullerene derivatives with physical and biological properties interesting for biomedicine and materials science [2]. The covalent linkage of C60 to moieties, such as porphyrins [3], anionic polymethine cyanine [4], and other bioactive molecules such as amino acids [5], peptides [6

Surface functionalization of aluminosilicate nanotubes with organic molecules

• Wei Ma,
• Weng On Yah,
• Hideyuki Otsuka and
• Atsushi Takahara

Beilstein J. Nanotechnol. 2012, 3, 82–100, doi:10.3762/bjnano.3.10

• can still be observed. This result is consistent with the explanation for the SFM observation. Terthiophene/imogolite hybrid Grafting of functionalized molecules (porphyrins, phtalocyanines, viologens, rhodamine B, etc.) onto metal-oxide surfaces of SiO2, TiO2, ITO, WO3, and ZrO2 can induce the

Charge transport in a zinc–porphyrin single-molecule junction

• Mickael L. Perrin,
• Christian A. Martin,
• Ferry Prins,
• Ahson J. Shaikh,
• Rienk Eelkema,
• Jan H. van Esch,
• Jan M. van Ruitenbeek,
• Herre S. J. van der Zant and
• Diana Dulić

Beilstein J. Nanotechnol. 2011, 2, 714–719, doi:10.3762/bjnano.2.77

• -bias and the high-bias regime. Porphyrins are interesting for this purpose as they are complex, non-rodlike molecules, which can form different stable conformations [7][8], especially when functionalized with metal-bound axial pyridine ligands [9]. Using the mechanically controllable break-junction

Recrystallization of tubules from natural lotus (Nelumbo nucifera) wax on a Au(111) surface

• Sujit Kumar Dora and
• Klaus Wandelt

Beilstein J. Nanotechnol. 2011, 2, 261–267, doi:10.3762/bjnano.2.30

• and is a well known substrate for the study of self-assembly of a number of different organic molecules, e.g., long chain alkanes [12][13], both aliphatic and aromatic thiols [14][15][16], substituted porphyrins [17][18], substituted pyridines [19], 1-nitronapthalene [20], saccharin [21], substituted

Oriented growth of porphyrin-based molecular wires on ionic crystals analysed by nc-AFM

• Thilo Glatzel,
• Lars Zimmerli,
• Shigeki Kawai,
• Ernst Meyer,
• Leslie-Anne Fendt and
• Francois Diederich

Beilstein J. Nanotechnol. 2011, 2, 34–39, doi:10.3762/bjnano.2.4

• studies by non-contact atomic force microscopy (nc-AFM) were done on ionic crystals with adsorbed PTCDA [17][18][19][20][21][22], PTCDI [23] or C60 [24]. In the case of porphyrins, the growth [25][26][27] and electronic properties [28] of stable, monolayered molecular wires on KBr(001) with a length of up

• decoupling. Results and Discussion Cleaving KBr crystals in vacuum and annealing them at moderate temperatures results in the formation of wide terraces with step edges in [100] direction which can be as long as several hundred nanometers. Evaporating the cyano-porphyrins onto the bulk KBr(001) surface

• efficiencies with a broader wavelength range compared to silicon solar cells, such antennae systems are for example also of potential interest for hybrid solar cells that could operate under low or moderate light conditions. Furthermore, porphyrins are known to be very promising building blocks: They are not