215313-78-3Relevant academic research and scientific papers
Basic Photophysical Properties of meso-Bis(pyren-2-yl)porphyrin: An Isomer of Pyrene-Substituted Porphyrins
Tomita, Shohei,Hirabayashi, Kazunori,Shimizu, Toshio,Goto, Kenta,Sugiura, Ken-ichi
, p. 2182 - 2186 (2017)
The Suzuki-Miyaura coupling reaction of pyren-2-yl boronic acid ester with a meso-dibromodiphenylporphyrin derivative was carried out to give another pyrene-substituted porphyrin. The electrophilic substitution reaction occurred selectively on the porphyr
Push-pull quinoidal porphyrins
Smith, Martin J.,Blake, Iain M.,Clegg, William,Anderson, Harry L.
supporting information, p. 3648 - 3654 (2018/05/26)
A family of push-pull quinoidal porphyrin monomers has been prepared from a meso-formyl porphyrin by bromination, thioacetal formation, palladium-catalyzed coupling with malononitrile and oxidation with DDQ. Attempts at extending this synthesis to a push-
A quinoidal bis-phenalenyl-fused porphyrin with supramolecular organization and broad near-infrared absorption
Diev, Vyacheslav V.,Femia, Denise,Zhong, Qiwen,Djurovich, Peter I.,Haiges, Ralf,Thompson, Mark E.
supporting information, p. 1949 - 1952 (2016/02/12)
A bis-phenalenyl-fused porphyrin has been synthesized by thermal dehydro-aromatization reaction regioselectively as a single syn-isomer. X-ray crystal structure revealed that both phenalenyl units of this porphyrin have close π-π contacts forming continuous network of interacting porphyrin rings. A broad and intense NIR absorption can be attributed to quinoidal character of bis-phenalenyl-fused porphyrin.
Synthesis of trans-A2B2- and trans-A2BC-porphyrins with polar 4′-(dimethylamino)tolan-4-yl substituents, and a screening protocol for vapor-phase deposition on metal surfaces
Alberti, Mariza N.,Nowakowska, Sylwia,Tzirakis, Manolis D.,Nowakowski, Jan,Fesser, Petra,Schweizer, W. Bernd,Shchyrba, Aneliia,Thilgen, Carlo,Jung, Thomas A.,Diederich, Fran?ois
supporting information, p. 5705 - 5719 (2014/10/16)
The role of polar 4-[p-(dimethylamino)phenylethynyl]phenyl substituents, with a calculated dipole moment of 3.35 Debye, in the self-assembly of trans-A2B2- and A2BC-substituted porphyrins was explored in the solid state by X-ray crystallography, and on an Au(111) surface by scanning tunneling microscopy (STM). Our results demonstrate that the dipolar character of these substituents blocks the 2D self-assembly of porphyrins into larger ordered domains on Au(111) at low coverage, whereas antiparallel dipole - dipole interactions govern the molecular ordering in the crystal. The STM analysis revealed an adaptation of the conformation of the prochiral building blocks and a site-selectivity of the adsorption. We present a general protocol for testing the suitability of higher-molecular-weight compounds, such as porphyrins, to be deposited on surface by sublimation in ultra-high vacuum (UHV). This protocol combines classical methods of chemical analysis with typical surface science techniques.
FUSING PORPHYRINS WITH POLYCYCLIC AROMATIC HYDROCARBONS AND HETEROCYCLES FOR OPTOELECTRIC APPLICATIONS
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Page/Page column 35, (2012/02/05)
A compound that can be used as a donor material in organic photovoltaic devices comprising a non-activated porphyrin fused with one or more non-activated polycyclic aromatic rings or one or more non-activated heterocyclic rings can be obtained by a thermal fusion process. By heating the reaction mixture of non-activated porphyrins with non-activated polycyclic aromatic rings or heterocyclic rings to a fusion temperature and holding for a predetermined time, fusion of one or more polycyciic rings or heterocyclic rings to the non-activated porphyrin core in meso,β fashion is achieved resulting in hybrid structures containing a distorted porphyrin ring with annulated aromatic rings. The porphyrin core can be olygoporphyrins.
Porphyrins fused with unactivated polycyclic aromatic hydrocarbons
Diev, Vyacheslav V.,Schlenker, Cody W.,Hanson, Kenneth,Zhong, Qiwen,Zimmerman, Jeramy D.,Forrest, Stephen R.,Thompson, Mark E.
experimental part, p. 143 - 159 (2012/02/17)
A systematic study of the preparation of porphyrins with extended conjugation by meso,β-fusion with polycyclic aromatic hydrocarbons (PAHs) is reported. The meso-positions of 5,15-unsubstituted porphyrins were readily functionalized with PAHs. Ring fusion using standard Scholl reaction conditions (FeCl3, dichloromethane) occurs for perylene-substituted porphyrins to give a porphyrin β,meso annulated with perylene rings (0.7:1 ratio of syn and anti isomers). The naphthalene, pyrene, and coronene derivatives do not react under Scholl conditions but are fused using thermal cyclodehydrogenation at high temperatures, giving mixtures of syn and anti isomers of the meso,β-fused porphyrins. For pyrenyl-substituted porphyrins, a thermal method gives synthetically acceptable yields (>30%). Absorption spectra of the fused porphyrins undergo a progressive bathochromic shift in a series of naphthyl (λmax = 730 nm), coronenyl (λmax = 780 nm), pyrenyl (λmax = 815 nm), and perylenyl (λmax = 900 nm) annulated porphyrins. Despite being conjugated with unsubstituted fused PAHs, the β,meso-fused porphyrins are more soluble and processable than the parent nonfused precursors. Pyrenyl-fused porphyrins exhibit strong fluorescence in the near-infrared (NIR) spectral region, with a progressive improvement in luminescent efficiency (up to 13% with λmax = 829 nm) with increasing degree of fusion. Fused pyrenyl-porphyrins have been used as broadband absorption donor materials in photovoltaic cells, leading to devices that show comparatively high photovoltaic efficiencies.
VISIBLE/NIR PHOTODETECTORS
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Page/Page column 63-64, (2011/04/14)
Porphyrin compounds are provided. The compounds may further comprise a fused polycyclic aromatic hydrocarbon or a fused heterocyclic aromatic. Fused polycyclic aromatic hydrocarbon s and fused heterocyclic aromatics may extend and broaden absorption, and modify the solubility, crystallinity, and film-forming properties of the porphyrin compounds. Additionally, devices comprising porphyrin compounds are also provided. The porphyrin compounds may be used in a donor/acceptor configuration with compounds, such as C60.
Fused pyrene-diporphyrins: Shifting near-infrared absorption to 1.5 μm and beyond
Diev, Vyacheslav V.,Hanson, Kenneth,Zimmerman, Jeramy D.,Forrest, Stephen R.,Thompson, Mark E.
supporting information; experimental part, p. 5523 - 5526 (2010/10/03)
(Figure Presented) Sticking together: Direct fusion of pyrene rings with diporphyrins can be achieved without prior activation of aromatic rings. This simple method gives pyrene-diporphyrin hybrids (see picture, C (pyrene) red, C (porphyrin) dark blue, N light blue, Zn green) with a high near-infrared (NIR) absorption that reaches the wavelengths required for use in telecommunications.
Post-modification of meso-meso-linked porphyrin arrays by iridium and rhodium catalyses for tuning of energy gap
Chen, Jinping,Aratani, Naoki,Shinokubo, Hiroshi,Osuka, Atsuhiro
experimental part, p. 1126 - 1133 (2010/04/23)
meso-meso-Linked diporphyrins fabricated with multiple unsaturated carboxylic acid groups are efficiently synthesized by the use of transition-metal catalysis. Iridium-catalyzed direct borylation of meso-meso-linked diporphyrins furnish multi-borylated di
