220355-86-2Relevant academic research and scientific papers
Synthesis of a porphyrin-hexaarylbenzene-hexabenzocoronene triad
Martin, Max M.,Jux, Norbert
, p. 454 - 460 (2018)
The synthesis of a triad consisting of porphyrin and hexabenzocoronene (HBC) units, which are connected via a central hexaarylbenzene (HAB) core, is presented. The ortho substitution pattern at the core results in a close proximity of the two chromophores, which influences their properties such as the intensity ratio of UV-vis absorption bands.
Efficient one-pot synthesis of rotaxanes bearing electron donors and [60]fullerene
Meglatto Jr., Jackson D.,Spencer, Robert,Schuster, David I.
, p. 4152 - 4155 (2009)
An easy one-pot procedure to synthesize rotaxanes bearing electron donors and C60 is described. The straightforward strategy, based on copper(I)-templated synthesis and "click" chemistry, proved to be very efficient and versatile, allowing the
Electronic Communication across Porphyrin Hexabenzocoronene Isomers
Martin, Max M.,Lungerich, Dominik,Haines, Philipp,Hampel, Frank,Jux, Norbert
supporting information, p. 8932 - 8937 (2019/05/29)
Single-molecule electronic components (SMECs) are envisioned as next-generation building blocks in quantum circuit systems. However, challenges such as the reproducibility of the electrode attachment to the individual molecules hamper their fundamental in
Triazole linked ruthenium(II)-porphyrin: Influence of the connectivity pattern on photophysical and electrochemical properties
Arora, Smriti,Nagpal, Ritika,Chauhan, Prashant,Chauhan, Shive Murat Singh
, p. 8878 - 8885 (2016/10/11)
Herein a copper catalysed click reaction has been used to covalently link π-conjugated 1,2,3-triazolyl zinc(ii) porphyrin and ruthenium(ii) bipyridyl with a single change in their connection through the linker. The properties of these compounds have been compared with the porphyrin-ruthenium(ii) tris(bipyridine) and ruthenium(ii) trisbipyridine complexes. Extensive photophysical and electrochemical studies reveal that changes in the electronic properties of the conjugates are a consequence of the different connectivity patterns with regular and inverse triazolyl-pyridyl moieties.
Systematic variation of cyanobuta-1,3-dienes and expanded tetracyanoquinodimethane analogues as electron acceptors in photoactive, rigid porphyrin conjugates
Urner, Lorenz M.,Sekita, Michael,Trapp, Nils,Schweizer, W. Bernd,W?rle, Michael,Gisselbrecht, Jean-Paul,Boudon, Corinne,Guldi, Dirk M.,Diederich, Franois
supporting information, p. 91 - 108 (2015/02/19)
We report on a homologous series of nine electron donor-acceptor systems featuring push-pull chromophores as electron acceptors, which are accessible by a cycloaddition-retroelectrocyclization (CA-RE) reaction. The conjugates comprise a ZnII porphyrin as electron donor, which is connected through either a rigid phenylene-ethynylene-phenylene (PEP)-bicyclo[2.2.2]octane or a PEP-trans-decahydroquinoline spacer to different anilino-substituted multicyanobutadienes or extended tetracyanoquinodimethane analogues with first reduction potentials ranging from-1.78 to-0.58 V vs. Fc+/Fc. Characterization of the conjugates includes X-ray crystallography, electrochemistry, DFT calculations, and fluorescence spectroscopy. The extent of ZnII porphyrin fluorescence quenching correlates with the strength of the electron acceptor. Overall, we demonstrate the synthetic feasibility of rationally modulating the acceptor strength by means of the CA-RE reaction in geometrically well-defined electron donor-acceptor conjugates.
Simultaneous occurrence of three different valence tautomers in meso -vinylruthenium-modified zinc porphyrin radical cations
Chen, Jing,Wuttke, Evelyn,Polit, Walther,Exner, Thomas,Winter, Rainer F.
supporting information, p. 3391 - 3394 (2013/05/08)
The mixed-valent radical cation of a styrylruthenium-modified meso-tetraarylzinc porphyrin forms a mixture of three different valence tautomers (VTs) in CH2Cl2 or 1,2-C2H 4Cl2 solutions. One of these
Triazole bridges as versatile linkers in electron donor-acceptor conjugates
De Miguel, Gustavo,Wielopolski, Mateusz,Schuster, David I.,Fazio, Michael A.,Lee, Olivia P.,Haley, Christopher K.,Ortiz, Angy L.,Echegoyen, Luis,Clark, Timothy,Guldi, Dirk M.
, p. 13036 - 13054 (2011/10/07)
Aromatic triazoles have been frequently used as π-conjugated linkers in intramolecular electron transfer processes. To gain a deeper understanding of the electron-mediating function of triazoles, we have synthesized a family of new triazole-based electron donor-acceptor conjugates. We have connected zinc(II)porphyrins and fullerenes through a central triazole moiety-(ZnP-Tri-C60)-each with a single change in their connection through the linker. An extensive photophysical and computational investigation reveals that the electron transfer dynamics-charge separation and charge recombination-in the different ZnP-Tri-C60 conjugates reflect a significant influence of the connectivity at the triazole linker. Except for the m4m-ZnP-Tri-C6017, the conjugates exhibit through-bond photoinduced electron transfer with varying rate constants. Since the through-bond distance is nearly the same for all the synthesized ZnP-Tri-C60 conjugates, the variation in charge separation and charge recombination dynamics is mainly associated with the electronic properties of the conjugates, including orbital energies, electron affinity, and the energies of the excited states. The changes of the electronic couplings are, in turn, a consequence of the different connectivity patterns at the triazole moieties.
Optimizing reaction conditions for synthesis of electron donor-[60]fullerene interlocked multiring systems
Megiatto Jr., Jackson D.,Spencer, Robert,Schuster, David I.
, p. 1544 - 1550 (2011/10/05)
Reaction conditions have been developed for the preparation of a series of rotaxanes and catenanes with appended electron-donor and electron-acceptor ([60]fullerene) subunits using a straightforward one-pot procedure based on Cu(i)-template synthesis and
A light-harvesting array composed of porphyrins and rigid backbones
Kozaki, Masatoshi,Uetomo, Atsuhiro,Suzuki, Shuichi,Okada, Keiji
supporting information; experimental part, p. 4477 - 4480 (2009/05/07)
(Chemical Equation Presented) A light-harvesting array containing rigid backbones, peripherally positioned Zn-porphyrin terminals, and a free-base (Fb) porphyrin core was prepared by a convergent method where the Sonogashira coupling reaction was used in the key steps. Effective intramolecular singlet-energy transfer from the peripheral Zn-porphyrin units to the Fb porphyrin core was observed. The efficiency of the energy transfer was compared with those of reference compounds.
