Papers by Giovanni Bottari
Turkish Journal of Chemistry, 2014
In this communication, encapsulation studies between metallosupramolecular capsule 1, formed by 2... more In this communication, encapsulation studies between metallosupramolecular capsule 1, formed by 2 subphthalocyanines (SubPcs) coordinated to 3 metallic centers, and phthalocyanine (Pc)-C 60 fullerene conjugates 2-5 have been carried out. It was shown that the encapsulation of the C 60 moiety by the SubPc cage occurred exclusively for dyads 2-4, whereas it was not observed in the case of triad 5. The rigidity of the linker between the Pc and the fullerene unit proved to have an important impact in the complex formation. Complex formation was tested in 2 different solvents, where the importance of solvophobic effects was highlighted. The resulting multicomponent supramolecular systems represent a unique combination of photoactive moieties where covalent and supramolecular chemistry coexist.
“Organic Nanomaterials: Synthesis, Characterization, and Device Applications”, Editors: Tomás Torres and Giovanni Bottari, John Wiley & Sons, Inc., Hoboken, New Jersey, 2013, ISBN: 978-1-118-01601-5
In the last decade, much progress has been made in the field of organic nanomaterials. Recent dev... more In the last decade, much progress has been made in the field of organic nanomaterials. Recent developments in nanoscience and nanotechnology have driven this field forward, thus allowing the preparation of novel materials with controlled morphology and well-defined properties, with clear and exciting technological applications. The new insights into the optoelectronic properties of molecules, together with the recent development of techniques such as scanning probe microscopy, among many others, have pushed chemists to design novel molecular and supramolecular functional architectures. The implications range from the basic molecular self-assembly of complementary organic systems, which constitute an important part of the so-called “bottom-up approach,” to exciting new applications of pure organic or hybrid materials, like the ones expected for low dimensional carbon nanostructures, such as fullerenes, nanotubes, and graphenes, or the recent developments in molecular photovoltaics,—f...
Chem. Commun., 2014
The unprecedented ultrasound-induced transformation of fluorescent organic nanoparticles based on... more The unprecedented ultrasound-induced transformation of fluorescent organic nanoparticles based on a molecular rotor into rhomboidal nanocrystals with enhanced stability and increased emission is presented.
Journal of the American Chemical Society, 2006
Chemical Communications, 2004
Melting points (m.p.) were determined in a Büchi 504392-S equipment and are uncorrected. UV/vis s... more Melting points (m.p.) were determined in a Büchi 504392-S equipment and are uncorrected. UV/vis spectra were recorded with a Hewlett-Packard 8453 instrument. IR spectra were recorded on a Bruker Vector 22 spectrophotometer. MALDI-TOF MS spectra and MALDI-TOF MS-MS spectra were obtained from a Applied Biosystem 4700 instrument equipped with a Nd:YAG laser operating at 355 nm. Elemental analysis were performed with a Perkin-Elmer 2400 CHN equipment. Column chromatography was carried out on silica gel Merck-60 (230-400 mesh, 60Ǻ). Analytical thin layer chromatography (TLC) was performed on aluminium sheets precoated with silica gel 60 F-254 from Merck. Size-exclusion chromatography was carried out using Bio-Beads S-X1 Beads (200-400 mesh) from BIO-RAD. Chemicals and solvents were purchased from commercial suppliers (Aldrich, Fluka, Strem, Acros, Fischer) and used without further purification. Iodo-substituted ZnPc 2, tri-tertbutylethynylphthalocyaninatozinc(II) and ZnPc dimer 3 were prepared following a reported procedure. 1 ZnPc-containing hexasubstituted benzene 1 was obtained as a mixture of regioisomers and characterized as such.
The Journal of Physical Chemistry Letters
Light‐Harvesting Properties of a Subphthalocyanine Solar Absorber Coupled to an Optical Cavity
Solar RRL
Chemical Science
Singly and doubly porphyrin-capped graphene nanoribbon segments are reported and their electronic... more Singly and doubly porphyrin-capped graphene nanoribbon segments are reported and their electronic properties are studied by high-resolution scanning tunneling microscopy and spectroscopy, and DFT calculations.
Bottom‐up Fabrication and Atomic‐Scale Characterization of Triply Linked, Laterally π‐Extended Porphyrin Nanotapes**
Angewandte Chemie International Edition
Expanding the Chemical Space of Tetracyanobuta‐1,3‐diene (TCBD) through a Cyano‐Diels‐Alder Reaction: Synthesis, Structure, and Physicochemical Properties of an Anthryl‐fused−TCBD Derivative
Chemistry – A European Journal
Porphyrin nanotapes (Por NTs) have attracted vast interest as potential molecular wires thanks to... more Porphyrin nanotapes (Por NTs) have attracted vast interest as potential molecular wires thanks to their exceptional electronic properties. Recently, Por NTs have been synthesized by solution-based methods, demonstrating high versatility and great potential for technological applications. However, their synthesis is tedious and their characterization limited by low solubility and stability. Here, we report the first example of meso-meso triply-fused Por NTs, which are prepared from a readily available Por precursor through a two-step synthesis on Au(111). The structural and electronic properties of individual Por NTs are addressed, both on Au(111) and on a thin insulating NaCl layer, by high-resolution scanning probe microscopy/spectroscopy complemented by density functional theory calculations.
An exciting twenty-year journey exploring porphyrinoid-based photo- and electro-active systems
Coordination Chemistry Reviews
Herein, we present a simple and straightforward method for the synthesis of phenalenyl-fused Pors... more Herein, we present a simple and straightforward method for the synthesis of phenalenyl-fused Pors (Por A0, PorA2 and PorA4) through readily available molecular precursors. While PorA0 was prepared by “wet” synthesis, the two- and four-fold phenalenyl-fused Por derivatives PorA2 and PorA4 were fabricated through a surface-assisted cyclodehydrogenation reaction from meso-2,6-dimethylphenyl(dmp) substituted precursors Por(dmp)2 and Por(dmp)4, respectively. In a systemat-ic way, we examined the structural and electronic properties of three surface-supported Pors.
Enabling Racemization of Axially Chiral Subphthalocyanine–Tetracyanobutadiene–Aniline Enantiomers by Triplet State Photogeneration
Angewandte Chemie
Angewandte Chemie International Edition
Die selektive Synthese … …e ines Porphyrin/Graphen-Nanoband-Hybrids auf einer Oberfläche wird von... more Die selektive Synthese … …e ines Porphyrin/Graphen-Nanoband-Hybrids auf einer Oberfläche wird von S. Decurtins,G .B ottari, R. Fasel, T. Torres et al. in ihrem Forschungsartikel auf S. 1350 beschrieben. Seine atomar präzise Struktur wurde eindeutig mittels bindungsaufgelçster Rastertunnelmikroskopie und Nicht-Kontakt-Rasterkraftmikroskopie charakterisiert, während elektronische Eigenschaften mit Rastertunnelspektroskopieu nd DFT-Rechnungen untersucht wurden. Grafik:Roland Wilkins.
Chemical Science
Two subphthalocyanines (SubPcs) decorated at their peripheral (SubPc 1) or peripheral and axial (... more Two subphthalocyanines (SubPcs) decorated at their peripheral (SubPc 1) or peripheral and axial (SubPc 2) positions with tetracyanobuta-1,3-diene (TCBD)-aniline moieties have been prepared as novel electron donor-acceptor (D−A) conjugates. In...
Evidence of charge-remote fragmentation in protonated [60]fulleropyrrolidine multi-adducts
International Journal of Mass Spectrometry
Protonation-Induced Changes in the Photophysical Properties of a Phthalocyanine and a Covalently-Linked, Phthalocyanine-C60 Fullerene Dyad
ECS Journal of Solid State Science and Technology
Subphthalocyanines Axially Substituted with a Tetracyanobuta-1,3-diene-Aniline Moiety: Synthesis, Structure, and Physicochemical Properties
Journal of the American Chemical Society, Apr 6, 2017
A 1,1,4,4-tetracyanobuta-1,3-diene (TCBD)-aniline moiety has been introduced, for the first time,... more A 1,1,4,4-tetracyanobuta-1,3-diene (TCBD)-aniline moiety has been introduced, for the first time, at the axial position of two subphthalocyanines (SubPcs) peripherally substituted with hydrogen (H12SubPc) or fluorine atoms (F12SubPc). Single-crystal X-ray analysis of both SubPc-TCBD-aniline systems showed that each conjugate is a racemic mixture of two atropisomers resulting from the almost orthogonal geometry adopted by the axial TCBD unit, which were separated by chiral high-performance liquid chromatography. Remarkably, the single-crystal X-ray structure of one atropisomer of each SubPc-TCBD-aniline conjugate has been solved, allowing to unambiguously assign the atropisomers' absolute configuration, something, to the best of our knowledge, unprecedented in TCBD-based conjugates. Moreover, the physicochemical properties of both SubPc-TCBD-aniline racemates have been investigated using a wide range of electrochemical as well as steady-state and time-resolved spectroscopic techn...
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Papers by Giovanni Bottari