The synthesis, photophysical properties and application as emitters in solution-processed multi-layer organic light-emitting diodes (OLEDs) of a series of blue-green to red light-emitting phosphorescent platinum(II) complexes are reported. These complexes consist of phenylisoquinoline, substituted phenylpyridines or tetrahydroquinolines as C^N cyclometalating ligands and dipivaloylmethane as an ancillary ligand. Depending on both the structure of the C^N cyclometalating ligands and the dopant concentration in the matrix, these platinum(II) complexes exhibit different aggregation tendencies. This property affects the photoluminescence spectra of the investigated compounds and colour-stability of the fabricated OLEDs. Using the blue-green to yellow-green emitting complexes, the best results were obtained with the 2-(4-trifluoromethylphenyl)-5,6,7,8-tetrahydroquinoline based platinum(II) complex. A maximum luminous efficiency of 4.88 cd A(-1) and a power efficiency of 4.65 lm W(-1), respectively, were achieved. Employing the red emitting phenylisoquinoline based complex as an emitter, colour-stable and efficient (4.71 cd A(-1), 5.12 lm W(-1)) devices were obtained.

The synthesis and photophysical properties of a series of yellow-green to blue-green emitting heteroleptic, cyclometalated Pt(II)(acac) complexes based on substituted phenylpyridine and tetrahydroquinoline ligands is reported. The luminescence intensities and lifetimes of these compounds were also studied in poly(styrene) films with respect to their responses to oxygen and temperature. Particularly, due to the insensitivity to oxygen quenching, these complexes are promising candidates as inert reference dyes in optical sensors. On the other hand, the Pt(II) complex with 2-(4-bromophenyl)-5,6,7,8-tetrahydroquinoline as C^N ligand, displays a strong temperature quenching effect. The distinct response to temperature was additionally calibrated after incorporation in poly(vinylidene chloride-co-acrylonitrile) serving as oxygen-blocking matrix copolymer. The resulting yellow-green-emitting temperature sensor signifies an interesting alternative to the available mostly red emitting temperature-sensitive probes.

An electrospray ionization quadrupole time-of-flight mass spectrometer has been utilized to investigate the relative ligand-binding strengths in a series of heteroleptic-charged iridium(III) complexes of the general formula [(C^N)(2) Ir(III) (S-tpy)](PF(6) ) by using variable collision energies. Collision-induced dissociation experiments were performed in order to study the stability of the Ir(III) complexes that are, for instance, suitable phosphors in light-emitting electrochemical cells. The ratio of signal intensities belonging to the fragment and the undissociated complex depends on the collision energy applied for the tandem mass spectra (MS/MS) analysis. By defining the threshold collision energy and the point of complete complex dissociation, it is possible to estimate the relative complex stabilities depending on the nature of the coordinated ligands [i.e. type of cyclometalating ligand (C^N), substituents on the S-shaped terpyridine (S-tpy)]. The collision energy values differed as a function of the coordination sphere of the Ir(III) centers.

The first fluorescent material for the referenced simultaneous RGB (red green blue) imaging of barometric pressure (oxygen partial pressure) and temperature is presented. This sensitive coating consists of two platinum(II) complexes as indicators and a reference dye, each of which is incorporated in appropriate polymer nanoparticles. These particles are dispersed in a polyurethane hydrogel and spread onto a solid support. The emission of the (oxygen) pressure indicator, PtTFPP, matches the red channel of a RGB color camera, whilst the emission of the temperature indicator [Pt(II) (Br-thq)(acac)] matches the green channel. The reference dye, 9,10-diphenylanthracene, emits in the blue channel. In contrast to other dual-sensitive materials, this new coating allows for the simultaneous imaging of both indicator signals, as well as the reference signal, in one RGB color picture without having to separate the signals with additional optical filters. All of these dyes are excitable with a 405 nm light-emitting diode (LED). With this new composite material, barometric pressure can be determined with a resolution of 22 mbar; the temperature can be determined with a resolution of 4.3 °C.

The modular approaches towards 2,2':6',2 ''-terpyridines and U-/S-shaped terpyridines are combined to yield a new family of ditopic ligands. Functionalized Krohnke-type terpyridines were used as key building blocks for the construction of hetero-bis(terpyridine)s. The described compounds might serve as new templates for the self-assembly towards new metallosupramolecular functional materials.

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A highly efficient domino reaction starting from tetrahydroquinolinone and a series of bisiminium salts provides the corresponding bis(U-terpyridines). These ligands have been treated with [(tpy)RuCl3] to afford novel dinuclear complexes [(tpy)Ru(L)Ru(tpy)]4+. The protocol is also applied for the synthesis of a star-shaped tris(U-terpyridine) and the trinuclear complex [{(tpy)Ru}3(L)]6+. In view of potential applications in the fields of metallopolymers and molecular devices, the electronic spectra, as well as the electrochemical potentials of all the complexes have been obtained. According to these data, no significant intermetal interaction has been observed for the ruthenium complexes presented here.

Based on S-shaped terpyridines, a series of yellow, orange, and red-orange light-emitting iridium(iii) complexes has been synthesized. The respective compounds have been prepared by the bridge-splitting method starting from the dimeric precursor complexes [(ppy)2Ir-μ-Cl]2, [(ppy-CHO)2Ir-μ-Cl]2, and [(c6)2Ir-μ-Cl]2. The products have been fully characterized by one- and two-dimensional (1H–1H correlation) NMR spectroscopy, elemental analysis, and MALDI-TOF mass spectrometry revealing the successful coordination of the iridium(iii) centres to the S-shaped terpyridine ligands. Furthermore, the quantitative coordination has been verified by the photophysical and electrochemical properties of the mononuclear iridium(iii) complexes. The photoluminescence spectra have shown strong emissions with maxima between 538 and 600 nm. The study of the optical properties of these novel complexes has indicated that the colour shifts are mainly depending on the nature of the cyclometallating ligands.

Angewandte ChemieVolume 94, Issue 12 p. 926-926 Zuschriften Synthese speziell substituierter 1-Azaadamantane Dr. Nikolaus Risch, Fakultät für Chemie der Universität Universitätsstraße, D-4800 BielefeldSearch for more papers by this authorWolfgang Saak, Fakultät für Chemie der Universität Universitätsstraße, D-4800 BielefeldSearch for more papers by this author Dr. Nikolaus Risch, Fakultät für Chemie der Universität Universitätsstraße, D-4800 BielefeldSearch for more papers by this authorWolfgang Saak, Fakultät für Chemie der Universität Universitätsstraße, D-4800 BielefeldSearch for more papers by this author First published: Dezember 1982 https://doi.org/10.1002/ange.19820941216Citations: 7AboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article.Citing Literature Volume94, Issue12Dezember 1982Pages 926-926 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. RelatedInformation

Phosphonate-substituted iminium salt 2 was used in Mannich reactions with various nucleophiles to obtain novel alpha-aminophosphonates. This straightforward and efficient methodology has a broad scope and provides highly functionalized Mannich bases (4 and 8). Furthermore, vinylic, aromatic and homoallylic alpha-aminophosphonates (5, 10 and 12) were synthesized in good yields. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

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