464885-23-2Relevant articles and documents
Electronic Modulation of Terrylene Diimides Leading to Core-Twisting, Tunable Emission and Intermolecular Interactions
Regar, Ramprasad,Mehra, Kundan Singh,Bhowal, Rohit,Sankar, Jeyaraman
, p. 6278 - 6284 (2019/11/05)
Three new symmetrically para-phenylethynylene-substituted terrylene diimide derivatives namely, TDI-Ph, TDI-PhCN and TDI-PhNMe2 were synthesized to study the electronic effects on the structure and properties. The solid-state single-crystal structures for TDI-Ph and TDI-PhCN as well as for the precursor TDI-Br4 are presented. The X-ray diffraction studies revealed twisting in the bay-area of terrylene core, which improved the solubility as well, despite of having some of the shortest intermolecular Br···Br and C-H···O interactions in TDI-Br4. All the compounds exhibited near infra-red absorption and emission except for TDI-PhNMe2; especially TDI-PhNMe2 showed interesting broad absorption ranging from 300 to 970 nm. Further, the effects of electron-donating and accepting unit on electrochemical and optical properties have been investigated.
The synthesis and aggregation-induced near-infrared emission of terrylenediimide-tetraphenylethene dyads
Xie, Nuo-Hua,Li, Chong,Liu, Jun-Xia,Gong, Wen-Liang,Tang, Ben Zhong,Li, Guigen,Zhu, Ming-Qiang
supporting information, p. 5808 - 5811 (2016/05/19)
We design and synthesize terrylenediimide-tetraphenylethene dyads, which exhibit featured aggregation-induced near-infrared fluorescence with a maximum emission wavelength of up to 800 nm.
New soluble near-infrared dyes based on terrylene diimides with four aromatic heterocycles
Wei, Huimin,Jiang, Nan,Zhao, Nan,Zhang, Ying,Gao, Baoxiang
supporting information, p. 356 - 360 (2014/05/20)
Terrylene diimides with four aromatic heterocycles (AHTDIs) were synthesized under Stille Cross-coupling conditions and fully characterized by NMR and mass spectrometry. The aggregation of the terrylene diimide (TDI) was suppressed by four heterocycles substituents on the bay region, and these AHTDIs exhibited good solubility in common organic solvents. The effects of the substituted groups on the optical and electrochemical properties were also investigated. The introduction of four aromatic heterocycles on the bay of TDI resulted in significant red-shifts of the absorption peak (100 nm), corresponding to a decrease in the band gap from 1.82 to 1.50 eV. Furthermore, with four rich electron aromatic heterocycles, the AHTDIs showed 280 mV negative-shifts of first oxidation potentials and a new oxidation wave, corresponding to an increase in the HOMO levels from?-5.60 to?-5.28 eV. Two soluble NIR dyes based on terrylene diimides were synthesized by the introduction of aromatic heterocycles substituents on the bay region. The effects of the substituted groups on the optical and electrochemical properties were further investigated. Copyright
Photoluminescent energy transfer from poly(phenyleneethynylene)s to near-infrared emitting fluorophores
Levine, Mindy,Song, Inja,Andrew, Trisha L.,Kooi, Steven E.,Swager, Timothy M.
scheme or table, p. 3382 - 3391 (2011/05/05)
Photoluminescent energy transfer was investigated in conjugated polymer-fluorophore blended thin films. A pentiptycene-containing poly(phenyleneethynylene) was used as the energy donor, and 13 fluorophores were used as energy acceptors. The efficiency of
Synthesis and modification of terrylenediimides as high-performance fluorescent dyes
Nolde, Fabian,Qu, Jianqiang,Kohl, Christopher,Pschirer, Neil G.,Reuther, Erik,Muellen, Klaus
, p. 3959 - 3967 (2007/10/03)
Two new synthetic approaches to terrylenediimides, highly photostable fluorescent dyes, are described. For the first time terrylenediimide has been synthesised in a straightforward procedure that makes large quantities available. The second route includes an efficient cross-coupling reaction followed by a cyclodehy-drogenation. Monofunctionalisation of the imide structure allows terrylenediimides now to be coupled with a variety of compounds, for example, by Suzuki cross-coupling, which can lead to an array of terrylenediimides with new functional groups such as hydroxy, amino, or carboxy groups needed to link up with other molecules. The functionalisation in the bay region is used to tune the properties of terrylenediimides and extend the range of applications, for example, by introducing water solubility. These tetrasubstituted terrylenediimides offer, depending on the substituents used, exciting features such as good solubility in common organic solvents, water solubility, or NIR absorption.
Synthesis and Characterization of Dendritic Multichromophores Based on Rylene Dyes for Vectorial Transduction of Excitation Energy
Weil, Tanja,Reuther, Erik,Beer, Cornelia,Muellen, Klaus
, p. 1398 - 1414 (2007/10/03)
The synthesis of dendritic multichromophores based on a rigid polyphenylene scaffold is presented. Different rylene chromophores are incorporated into the core, the branches, and the surface of the dendrimer. In this way, two generations of dendritic dyads consisting of a terrylenediimide core, a stiff polyphenylene scaffold, and a perylenemonoimide periphery were obtained. Furthermore, the first synthetic approach to a dendritic triad is introduced. The outer sphere of this macromolecule is formed by naphthalenemonoimide chromophores, whereas perylenemonoimide groups are located in the dendritic scaffold, and the terrylenediimide chromophore serves as a core molecule. This multichromophore absorbs over the whole range of the visible spectrum and shows well-separated absorption envelopes. In the course of dendrimer synthesis new attempts towards a straightforward functionalization strategy for rylene dyes are also presented.
1,6,9,14-TETRASUBSTITUTED TERRYLENE TETRACARBOXYLIC ACID DIIMIDES
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Page column 20-21, (2008/06/13)
The invention relates to 1,6,9,14-tetrasubstituted terrylene tetracarboxylic acid diimides of general formula (I), in which the variables are defined as follows: X, Y independently of one another represent bromium; cyano; aryloxy, arylthio, hetaryloxy or
