Double-decker lutetium phthalocyanine functionalized with 4-phenylthiazol-2-thiol moieties: Synthesis, characterization, electrochemistry, spectroelectrochemistry and electrochromism

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

Download Full-text

Steady state charge conduction through solution processed liquid crystalline lanthanide bisphthalocyanine films

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424619501918 ◽

2019 ◽

Vol 23 (11n12) ◽

pp. 1603-1615

Author(s):

Chandana Pal ◽

Isabelle Chambrier ◽

Andrew N. Cammidge ◽

A. K. Sharma ◽

Asim K. Ray

Keyword(s):

Metal Ions ◽

Liquid Crystalline ◽

Microscopy Study ◽

Individual Characteristics ◽

Central Metal ◽

Force Microscopy ◽

Atomic Force ◽

Double Decker ◽

Order Of Magnitude ◽

Chain Lengths

In-plane electrical characteristics of non-peripherally octyl(C[Formula: see text]H[Formula: see text]- and hexyl(C[Formula: see text]H[Formula: see text]-substituted liquid crystalline (LC) double decker lanthanide bisphthalocyanine (LnPc[Formula: see text] complexes with central metal ions lutetium (Lu), and gadolinium (Gd) have been measured in thin film formulations on interdigitated gold (Au) electrodes for the applied voltage ([Formula: see text] range of [Formula: see text]. The conduction mechanism is found to be Ohmic within the bias of [Formula: see text] while the bulk limited Poole–Frenkel mechanism is responsible for the higher bias. The compounds show individual characteristics depending on the central metal ions, substituent chain lengths and their mesophases. Values of 67.55 [Formula: see text]cm[Formula: see text] and 42.31 [Formula: see text]cm[Formula: see text] have been obtained for room temperature in-plane Ohmic conductivity of as-deposited octyl lutetium (C[Formula: see text]LuPc[Formula: see text] and hexyl gadolinium (C[Formula: see text]GdPc[Formula: see text] films, respectively while C[Formula: see text]GdPc[Formula: see text] films exhibit nearly two orders of magnitude smaller conductivity. On annealing at 80[Formula: see text]C, Ohmic conductivities of C[Formula: see text]LuPc[Formula: see text] and C[Formula: see text]GdPc[Formula: see text] are found to have increased but the conductivity of C[Formula: see text]GdPc[Formula: see text] decreased by more than one order of magnitude to 1.5 [Formula: see text]cm[Formula: see text]. For physical interpretation of the charge transport behavior of these three molecules, their UV-vis optical absorption spectra in the solution and in as-deposited and annealed solid phases and atomic force microscopy study have been performed. It is believed that both orientation and positional reorganizations are responsible, depending upon the size of the central ion and side chain length.

Download Full-text

Effects of Hydrogen Bonding on the Monolayer Properties of Amphiphilic Double-Decker-Shaped Polyhedral Silsesquioxanes

Langmuir ◽

10.1021/la2021726 ◽

2011 ◽

Vol 27 (14) ◽

pp. 9068-9068 ◽

Cited By ~ 4

Author(s):

Asuman C. Kucuk ◽

Jun Matsui ◽

Tokuji Miyashita

Keyword(s):

Hydrogen Bonding ◽

Double Decker

Download Full-text

Front Cover: Allosteric Guest Binding in Chiral Zirconium(IV) Double Decker Porphyrin Cages (Eur. J. Org. Chem. 4/2021)

European Journal of Organic Chemistry ◽

10.1002/ejoc.202001599 ◽

2021 ◽

Vol 2021 (4) ◽

pp. 512-512

Author(s):

Jeroen P. J. Bruekers ◽

Matthijs A. Hellinghuizen ◽

Nicolas Vanthuyne ◽

Paul Tinnemans ◽

Pieter J. Gilissen ◽

...

Keyword(s):

Front Cover ◽

Double Decker ◽

Guest Binding

Download Full-text

Synthesis of Silsesquioxanes with Substituted Triazole Ring Functionalities and Their Coordination Ability

Molecules ◽

10.3390/molecules26020439 ◽

2021 ◽

Vol 26 (2) ◽

pp. 439

Author(s):

Monika Rzonsowska ◽

Katarzyna Kozakiewicz ◽

Katarzyna Mituła ◽

Julia Duszczak ◽

Maciej Kubicki ◽

...

Keyword(s):

Ligand Binding ◽

Molecular Complex ◽

Coordination Compounds ◽

Triazole Ring ◽

Spectroscopic Characterization ◽

Process Conditions ◽

Double Decker ◽

Triazole Ligand ◽

Coordination Ability ◽

High Yields

A synthesis of a series of mono-T8 and difunctionalized double-decker silsesquioxanes bearing substituted triazole ring(s) has been reported within this work. The catalytic protocol for their formation is based on the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) process. Diverse alkynes were in the scope of our interest—i.e., aryl, hetaryl, alkyl, silyl, or germyl—and the latter was shown to be the first example of terminal germane alkyne which is reactive in the applied process’ conditions. From the pallet of 15 compounds, three of them with pyridine-triazole and thiophenyl-triazole moiety attached to T8 or DDSQ core were verified in terms of their coordinating properties towards selected transition metals, i.e., Pd(II), Pt(II), and Rh(I). The studies resulted in the formation of four SQs based coordination compounds that were obtained in high yields up to 93% and their thorough spectroscopic characterization is presented. To our knowledge, this is the first example of the DDSQ-based molecular complex possessing bidentate pyridine-triazole ligand binding two Pd(II) ions.

Download Full-text

Phosphorylated-calix[4]arene double-deckers of single rare earth metal ions

Chemical Communications ◽

10.1039/d1cc02910j ◽

2021 ◽

Author(s):

Marjan Hosseinzadeh ◽

Sergio Sanz ◽

Jan van Leusen ◽

Natalya V Izarova ◽

Euan K Brechin ◽

...

Keyword(s):

Rare Earth ◽

Metal Ions ◽

Rare Earth Metal ◽

Earth Metal ◽

Double Decker ◽

Organic Framework

Combination of phosphoryl and calix[4]arene moieties in the same organic framework (LPO) directs the formation of homoleptic double-decker complexes [LnIII(LPO)2](O3SCF3)3 for Ln = Tb and Dy, with the latter displaying...

Download Full-text

Electrochemically controlled multistability of ultrathin films of double-decker cerium phthalocyaninates

Russian Journal of Electrochemistry ◽

10.1134/s1023193512020164 ◽

2012 ◽

Vol 48 (2) ◽

pp. 218-233 ◽

Cited By ~ 6

Author(s):

S. L. Selector ◽

A. V. Shokurov ◽

V. V. Arslanov ◽

Yu. G. Gorbunova ◽

O. A. Raitman ◽

...

Keyword(s):

Ultrathin Films ◽

Double Decker

Download Full-text

Supramolecular structures of terbium(iii) porphyrin double-decker complexes on a single-walled carbon nanotube surface

RSC Advances ◽

10.1039/c9ra05818d ◽

2019 ◽

Vol 9 (48) ◽

pp. 28135-28145

Author(s):

Ahmed I. A. Abd El-Mageed ◽

Takuji Ogawa

Keyword(s):

Carbon Nanotubes ◽

Scanning Probe Microscopy ◽

Single Walled Carbon Nanotubes ◽

Supramolecular Structures ◽

Scanning Probe ◽

Single Walled Carbon Nanotube ◽

Single Walled Carbon ◽

Double Decker ◽

Walled Carbon Nanotubes ◽

First Time

For the first time, using scanning probe microscopy, the supramolecular structures of terbium porphyrin double-decker complexes were observed on single-walled carbon nanotubes surfaces, where the molecules formed a well-ordered self-assembled array.

Download Full-text