Fluorescent bioinspired albumin/polydopamine nanoparticles and their interactions with Escherichia coli cells

• Eloïse Equy,
• Jordana Hirtzel,
• Sophie Hellé,
• Béatrice Heurtault,
• Eric Mathieu,
• Morgane Rabineau,
• Vincent Ball and
• Lydie Ploux

Beilstein J. Nanotechnol. 2023, 14, 1208–1224, doi:10.3762/bjnano.14.100

• intrinsic fluorescence of bacteria under 405 nm excitation due to porphyrins [37][38]. With Ox-BSA/PDA NPs, no significant difference in fluorescence intensity could be detected in this emission range under 405 nm excitation compared to the intrinsic fluorescence background. This prevents a conclusion on

Two-dimensional molecular networks at the solid/liquid interface and the role of alkyl chains in their building blocks

• Suyi Liu,
• Yasuo Norikane and
• Yoshihiro Kikkawa

Beilstein J. Nanotechnol. 2023, 14, 872–892, doi:10.3762/bjnano.14.72

• between the core unit and aliphatic chains. When the meso positions of porphyrins were substituted with normal saturated alkyl chains (P-N), the porphyrin plane and the alkyl chain units exhibited torsional strain, resulting in a tilt angle between the porphyrin core and the direction of the alkyl chain

Molecular nanoarchitectonics: unification of nanotechnology and molecular/materials science

• Katsuhiko Ariga

Beilstein J. Nanotechnol. 2023, 14, 434–453, doi:10.3762/bjnano.14.35

• were successfully synthesized by sequential coupling of CF3-substituted copper, cobalt, and palladium porphyrins on the surface. The assembly of different porphyrin oligomers combines multiple functional properties such as gas adsorption and magnetism in a one-dimensional structure. This approach could

Cyclodextrins as eminent constituents in nanoarchitectonics for drug delivery systems

• Makoto Komiyama

Beilstein J. Nanotechnol. 2023, 14, 218–232, doi:10.3762/bjnano.14.21

• them, a linear polymer was constructed through consecutive inclusion of adamantane in β-CyD units. Upon further addition of poly(ethylene glycol) bearing adamantane at the terminus nanoparticles were formed (Figure 7B). In these nanoparticles, aggregation of porphyrins is suppressed because of steric

Design of surface nanostructures for chirality sensing based on quartz crystal microbalance

• Yinglin Ma,
• Xiangyun Xiao and
• Qingmin Ji

Beilstein J. Nanotechnol. 2022, 13, 1201–1219, doi:10.3762/bjnano.13.100

• enantiodiscrimination. Porphyrin derivatives. Porphyrins and metalloporphyrins have been proposed to be suitable hosts for chirality sensing due to their functionalization at peripheral positions of the framework and easily monitoring of structural changes by strong optical absorptions [79][80][81]. They may also be

• used as building blocks for organized materials expressing chirality at the supramolecular level [82][83]. The introduction of metal centers in porphyrins could further enhance the recognition interactions and form a more stable host–guest complex for chiral sensing [84]. For example, Simonneaux et al

• . reported a Ru-modified porphyrin as a chiral recognition host to achieve specific recognition of racemic isocyanides and alcohols [85]. Imai et al. and Hayashi et al. obtained chiral recognition of amino acids and peptides using Zn-modified porphyrins [86][87]. In general, the chirality of the porphyrin

Self-assembly of C₆₀ on a ZnTPP/Fe(001)–p(1 × 1)O substrate: observation of a quasi-freestanding C₆₀ monolayer

• Guglielmo Albani,
• Michele Capra,
• Alessandro Lodesani,
• Alberto Calloni,
• Gianlorenzo Bussetti,
• Marco Finazzi,
• Franco Ciccacci,
• Alberto Brambilla,
• Lamberto Duò and
• Andrea Picone

Beilstein J. Nanotechnol. 2022, 13, 857–864, doi:10.3762/bjnano.13.76

• ZnTPP directly on the bare Fe(001) surface results in a completely disordered film [47], therefore the passivation of Fe(001) with oxygen is a crucial step to obtain a suitable molecular buffer layer. Since porphyrins molecules lie flat on the Fe(001)–p(1 × 1)O surface, the ZnTPP wetting layer provides

• in UHV on a MgO(001) single crystal [48]. The Fe(001)–p(1 × 1)O surface was prepared by using the following procedure: the clean Fe substrate was exposed to 30 Langmuir of molecular oxygen at a pressure of = 2 × 10−7 mbar and subsequently annealed at about 700 °C for 5 min. Porphyrins were

• ZnTPP spectrum in Figure 3, the UPS peaks related to the main molecule ring and to the phenyl groups are labeled “R” and “Ph” [52][53], respectively, according to theoretical simulations performed on metal tetraphenyl porphyrins and metal porphyrins [54]. When an additional single layer of C60 is added

Self-assembly of amino acids toward functional biomaterials

• Huan Ren,
• Lifang Wu,
• Lina Tan,
• Yanni Bao,
• Yuchen Ma,
• Yong Jin and
• Qianli Zou

Beilstein J. Nanotechnol. 2021, 12, 1140–1150, doi:10.3762/bjnano.12.85

• conformational changes through various mechanisms, such as protonation, charge inversion, or chemical bond cleavage, promoting tumor-specific cellular uptake or drug release [82]. Sun et al. [83] coupled tryptophan-glycine (WG) to hydrophobic porphyrins (P) by an amidation reaction to obtain pH-responsive

• . [88] combined chemical reactions and manufactured bionic photobacteria based on self-assembly of amino acids and porphyrins. First, Fmoc-ʟ-Lys was self-assembled into a nanofiber template, then the ε-amino group on the surface of the Fmoc-ʟ-Lys fiber reacted with 3,4-dihydroxyphenylalanine (DOPA

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

• molecular design, the built-in functionality of the active part of the molecule can be preserved upon adsorption on a surface. An example of the preservation of catalytic properties is demonstrated for the redox behavior of manganese porphyrins at the solid–liquid interface. Redox reactions at the axial

Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu²⁺ ions

• Bahdan V. Ranishenka,
• Andrei Yu. Panarin,
• Irina A. Chelnokova,
• Sergei N. Terekhov,
• Peter Mojzes and
• Vadim V. Shmanai

Beilstein J. Nanotechnol. 2021, 12, 902–912, doi:10.3762/bjnano.12.67

• charged hydrophilic thiols (sodium 2-mercaptoethyl sulfonate, mercaptopropionic acid, 2-mercaptoethanol, 2-(dimethylamino)ethanethiol hydrochloride, and thiocholine) to vary the surface charge of the SERS substrate. We used two oppositely charged porphyrins, cationic copper(II) tetrakis(4-N-methylpyridyl

• functional group. We used a short ethylene linker and hydrophilic functional groups to avoid lipophilic interactions. Two hydrophilic porphyrins with similar structures, equal charge value and opposite charge (CuTMpyP4 and CuTSPP4) were used as model analytes. Structures of the modifying molecules and the

• with sodium mercaptoethyl sulfonate did not result in a significant change of the SERS intensity for both porphyrins (Figure 5, number 5). These data are in line with the initial negative charge of the NP surfaces. The high affinity of thiol groups to the Ag surface suggests that the chloride counter

Adsorption and self-assembly of porphyrins on ultrathin CoO films on Ir(100)

• Feifei Xiang,
• Tobias Schmitt,
• Marco Raschmann and
• M. Alexander Schneider

Beilstein J. Nanotechnol. 2020, 11, 1516–1524, doi:10.3762/bjnano.11.134

• Feifei Xiang Tobias Schmitt Marco Raschmann M. Alexander Schneider Solid State Physics, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), 91058 Erlangen, Germany 10.3762/bjnano.11.134 Abstract Porphyrins represent a versatile class of molecules, the adsorption behavior of which on solid

• islands on the 2BL film. The findings demonstrate the guiding effect of the cobalt oxide films of different thickness and the effect of functional surface anchoring. Keywords: adsorption energy; molecular rotors; porphyrins; self-assembly; transition metal oxides; Introduction Due to their variability

• with respect to functionalization and corresponding potential applications, porphyrins represent a fascinating class of molecules the properties of which at inorganic interfaces still have to be fully understood [1]. The investigation of adsorption properties and structures using surface science

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

• superstructure: Depending on the registry of the layer and substrate atoms, the surface is divided in areas of low and high local work function, denoted as “pores” and “wires”, respectively [28][29][30][31]. In recent years, our group and others used hBN/Cu(111) to guide the self-assembly of porphyrins [28][32

• ) [19]. The formation of extended domains for the pyrene derivatives 1–3 on hBN/Cu(111) even at a submonolayer coverage was reminiscent of findings for carbonitrile-functionalized porphyrins [38] and quaterphenylenes [36] but contrasted the site-selective adsorption on pore areas reported for TCNQ

Role of redox-active axial ligands of metal porphyrins adsorbed at solid–liquid interfaces in a liquid-STM setup

• Thomas Habets,
• Sylvia Speller and
• Johannes A. A. W. Elemans

Beilstein J. Nanotechnol. 2020, 11, 1264–1271, doi:10.3762/bjnano.11.110

• , Albert-Einstein-Straße 25, 18059 Rostock, Germany 10.3762/bjnano.11.110 Abstract In a liquid-STM setup environment, the redox behavior of manganese porphyrins was studied at various solid–liquid interfaces. In the presence of a solution of Mn(III)Cl porphyrins in 1-phenyloctane, which was placed at a

• ascribed to the occurrence of redox reactions in which chloride is oxidized to chlorine and the Mn(III) center of the porphyrin moiety is reduced to Mn(II). The resulting Mn(II) porphyrin products were identified by UV–vis analysis of the liquid phase. For solutions of Mn(III) porphyrins with non-redox

• active acetate instead of chloride axial ligands, the currents remained absent. Keywords: manganese; porphyrins; redox reactions; scanning tunneling microscopy; solid–liquid interface; Introduction Manganese(III) porphyrins are well-known catalysts for the epoxidation of alkenes [1][2][3][4]. The

A few-layer graphene/chlorin e6 hybrid nanomaterial and its application in photodynamic therapy against Candida albicans

• Selene Acosta,
• Carlos Moreno-Aguilar,
• Dania Hernández-Sánchez,
• Beatriz Morales-Cruzado,
• Erick Sarmiento-Gomez,
• Carla Bittencourt,
• Luis Octavio Sánchez-Vargas and
• Mildred Quintana

Beilstein J. Nanotechnol. 2020, 11, 1054–1061, doi:10.3762/bjnano.11.90

• visible light, and also should have a high absorption coefficient at a wavelength that penetrates cellular tissue [4]. In the visible electromagnetic spectrum, red light has the largest depth penetration into biological tissue [6][7]. Among different photosensitizers, porphyrins are heterocyclic molecules

• derived from four pyrrole-like subunits interconnected by methine groups [8]. Porphyrins possess all the characteristics of a good photosensitizer since they are planar or semiplanar molecules with π-electrons in a closed ring, resulting in a large conjugated system that strongly absorbs light in the

Rational design of block copolymer self-assemblies in photodynamic therapy

• Maxime Demazeau,
• Laure Gibot,
• Anne-Françoise Mingotaud,
• Patricia Vicendo,
• Clément Roux and
• Barbara Lonetti

Beilstein J. Nanotechnol. 2020, 11, 180–212, doi:10.3762/bjnano.11.15

• exhibiting polycyclic structures such as porphyrins (Figure 2), inorganic particles such as gold, or so-called upconverting nanoparticles. Developed in its modern form by Dougherty in the 1970’s [17], PDT is currently clinically employed in dermatology (e.g., for actinic keratinosis), ophthalmology (e.g

• porphyrins in the cavities of cyclodextrin was also proposed as driving force of amphiphilic self-assemblies [52][53][54]. A main drawback of this kind of nanosystems in which the photosensitizer is simply dissolved in the hydrophobic environment is the possible premature leakage during body circulation

• )methacrylamide) when irradiated at 680 nm [92]. Besides, the chelating properties of porphyrins towards ions such as Mn2+ [101] or Gd3+ [80] or 64Cu [99] can be used for magnetic resonant imaging (MRI). Oxygen self-compensation. Local tumor hypoxia is one of the issues of PDT as the inefficient oxygen supply

Molecular architectonics of DNA for functional nanoarchitectures

• Debasis Ghosh,
• Lakshmi P. Datta and
• Thimmaiah Govindaraju

Beilstein J. Nanotechnol. 2020, 11, 124–140, doi:10.3762/bjnano.11.11

• acid system is one of the distinct approaches to generate functional DNA architectures [88]. Porphyrins are well-known macrocyclic organic chromophores acting as light harvesting systems that can be efficiently compacted within the spatial arrangements of DNA double-helical assemblies [88]. Meunier [89

• ], Hélène [90], and co-workers reported the utility of porphyrin-tethered DNA as artificial nucleases. Murashima, Sugimoto, and co-workers adopted a novel approach to design DNA nanoarchitectures by substituting the nucleobases of DNA with porphyrins [91]. The tetraphenylporphyrin-modified nucleotide was

Advanced hybrid nanomaterials

• Andreas Taubert,
• Fabrice Leroux,
• Pierre Rabu and
• Verónica de Zea Bermudez

Beilstein J. Nanotechnol. 2019, 10, 2563–2567, doi:10.3762/bjnano.10.247

• operate in the physiological range with suitable sensitivity. Another metal–organic framework (MOF) is studied in “The nanoscaled metal–organic framework ICR-2 as a carrier of porphyrins for photodynamic therapy” [36]. Phosphinate-based MOF nanoparticles are decorated with porphyrin-type molecules as

Materials nanoarchitectonics at two-dimensional liquid interfaces

• Katsuhiko Ariga,
• Michio Matsumoto,
• Taizo Mori and
• Lok Kumar Shrestha

Beilstein J. Nanotechnol. 2019, 10, 1559–1587, doi:10.3762/bjnano.10.153

The effect of translation on the binding energy for transition-metal porphyrines adsorbed on Ag(111) surface

• Luiza Buimaga-Iarinca and
• Cristian Morari

Beilstein J. Nanotechnol. 2019, 10, 706–717, doi:10.3762/bjnano.10.70

• contains 18 electrons along the shortest cycle path. Consequently, the 4n + 2 Hückel rule is expected to play a key role in all their properties [2]. The applications of porphyrins in nanotechnology are related mainly to the structures formed after deposition on various substrates. A long list of

• applications can be found in the literature, ranging from molecular sensors [3] over memory devices [4] to light-harvesting structures [5][6][7]. Among all porphyrin compounds, transition-metal porphyrins (TMPPs) are of particularly interest. Because they accommodate a transition-metal atom in the center, the

• theoretical [24][25][26] attention. Among the coinage metals typically used for applications, Ag(111) has attracted particular interest [27][28][29]. A complex behavior of the porphyrins on this surface was shown. Parallel orientation with respect to the surface is preferred for sub-monolayer coverage, while

The nanoscaled metal-organic framework ICR-2 as a carrier of porphyrins for photodynamic therapy

• Jan Hynek,
• Sebastian Jurík,
• Martina Koncošová,
• Jaroslav Zelenka,
• Ivana Křížová,
• Tomáš Ruml,
• Kaplan Kirakci,
• Ivo Jakubec,
• František Kovanda,
• Kamil Lang and
• Jan Demel

Beilstein J. Nanotechnol. 2018, 9, 2960–2967, doi:10.3762/bjnano.9.275

• characterised phosphinate-based MOF nanoparticles, nanoICR-2 (Inorganic Chemistry Rez). We demonstrate that nanoICR-2 can be decorated with anionic 5,10,15,20-tetrakis(4-R-phosphinatophenyl)porphyrins (R = methyl, isopropyl, phenyl) by utilizing unsaturated metal sites on the nanoparticle surface. The use of

• these porphyrins allows for superior loading of the nanoparticles when compared with commonly used 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin. The nanoICR-2/porphyrin composites retain part of the free porphyrins photophysical properties, while the photodynamic efficacy is strongly affected by the R

• ]. Singlet oxygen is a short-lived, highly oxidative species with bactericidal and virucidal properties [6]. The cytotoxic effect can be intentionally employed in anticancer treatment in the form of photodynamic therapy (PDT) [7][8]. The most commonly utilised photosensitizers in PDT are porphyrins or

Heterostuctures of 4-(chloromethyl)phenyltrichlorosilane and 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine prepared on Si(111) using particle lithography: Nanoscale characterization of the main steps of nanopatterning

• Phillip C. Chambers and
• Jayne C. Garno

Beilstein J. Nanotechnol. 2018, 9, 1211–1219, doi:10.3762/bjnano.9.112

• porphyrins and organosilanes. A protocol was developed with particle lithography using steps of immersion in organosilane solutions to selectively passivate the surface of Si(111) with octadecyltrichlorosilane (OTS). A methyl-terminated matrix was chosen to direct the growth of CMPS nanostructures to fill

• . Nanostructures of CMPS formed within the nanoholes, to furnish spatially selective sites for binding porphyrins. The samples were then characterized with AFM to evaluate the height and morphology of the CMPS nanostructures that had formed within the nanoholes of OTS. The samples were then refluxed in a porphyrin

• solution for selective binding to produce heterostructures. The attachment of porphyrins was evidenced by increases in the height and width of the CMPS nanopatterns. The measurements of size indicate that multiple layers of porphyrins were added. Through each step of the surface reaction the surrounding

Review on nanoparticles and nanostructured materials: history, sources, toxicity and regulations

• Jaison Jeevanandam,
• Ahmed Barhoum,
• Yen S. Chan,
• Alain Dufresne and
• Michael K. Danquah

Beilstein J. Nanotechnol. 2018, 9, 1050–1074, doi:10.3762/bjnano.9.98

Adsorption of iron tetraphenylporphyrin on (111) surfaces of coinage metals: a density functional theory study

• Hao Tang,
• Nathalie Tarrat,
• Véronique Langlais and
• Yongfeng Wang

Beilstein J. Nanotechnol. 2017, 8, 2484–2491, doi:10.3762/bjnano.8.248

• spin switches. Keywords: activation barrier; density functional theory; iron tetraphenylporphyrin; spin switch; spin states; Introduction Porphyrins, phthalocyanines and their transition-metal (TM) complexes are largely investigated in surface science as reported in detail by Gottfried [1]. The

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

(Metallo)porphyrins for potential materials science applications

• Lars Smykalla,
• Carola Mende,
• Michael Fronk,
• Pablo F. Siles,
• Michael Hietschold,
• Georgeta Salvan,
• Dietrich R. T. Zahn,
• Oliver G. Schmidt,
• Tobias Rüffer and
• Heinrich Lang

Beilstein J. Nanotechnol. 2017, 8, 1786–1800, doi:10.3762/bjnano.8.180

• use discrete (metallo)porphyrins for the formation of (sub)monolayers by surface-confined polymerization, of monolayers formed by supramolecular recognition and of thin films formed by sublimation techniques. Selected physical properties of these systems are reported as well. The application potential

• of those ensembles of (metallo)porphyrins in materials science is discussed. Keywords: atomic force microscopy; magneto-optical Kerr effect spectroscopy; scanning tunnelling microscopy and spectroscopy; self-assembly; surface-confined 2D polymerization; transport properties; Review Introduction

• Macrocyclic compounds occurring in nature play an essential role in biological and chemical processes, whereby porphyrins and their corresponding metal species rank among the most frequently occurring and important representatives [1][2][3]. In addition, there is a plethora of synthetic possibilities to

Synthesis, spectroscopic characterization and thermogravimetric analysis of two series of substituted (metallo)tetraphenylporphyrins

• Rasha K. Al-Shewiki,
• Carola Mende,
• Roy Buschbeck,
• Pablo F. Siles,
• Oliver G. Schmidt,
• Tobias Rüffer and
• Heinrich Lang

Beilstein J. Nanotechnol. 2017, 8, 1191–1204, doi:10.3762/bjnano.8.121

• yields exceeding 80%. The porphyrins 2 and 3 could be converted to the corresponding metalloporphyrins MTPP(C(O)NR2)4 (R = Me/iPr for M = Zn (2a, 3a); Cu (2b, 3b); Ni (2c, 3c); Co (2d, 3d)) by the addition of 3 equiv of anhydrous MCl2 (M = Zn, Cu, Ni, Co) to dimethylformamide solutions of 2 and 3 at

• elevated temperatures. Metalloporphyrins 2a–d and 3a–d were obtained in yields exceeding 60% and have been, as well as 2 and 3, characterized by elemental analysis, electrospray ionization mass spectrometry (ESIMS) and IR and UV–vis spectroscopy. Porphyrins 2, 2a–d and 3, 3a–d are not suitable for organic

• porphyrins of the type H2TPP(OH)4 (tetra(p-hydroxyphenyl)porphyrin) [6][7] and MTPP(OMe)4/H2TPP(OMe)4 (tetra(p-methoxyphenyl)porphyrin) (M = Cu [8][9], Ni [9]), cf. Figure 1. The properties of the metalloporphyrins are governed by the (transition) metal ions and the exocyclic moieties on the individual