100125-12-0Relevant articles and documents
Preparation of symmetric dibromides of 1,10-phenanthroline
Saitoh, Yutaka,Koizumi, Take-Aki,Osakada, Kohtaro,Yamamoto, Takakazu
, p. 1336 - 1339 (1997)
Bromation of 1,10-phenanthroline with Br2 proceeds smoothly in the presence of S2Cl2 and pyridine to give 3,8-dibromo-1,10-phenanthroline in good yield. Bromation of 2,9-dibutoxy-1,10-phenanthroline with Br2 in
Photobiological activity of Ru(ll) dyads based on (Pyren-1 -yl)ethynyl derivatives of 1, 10-Phenanthroline
Monro, Susan,Scott, John,Chouai, Abdellatif,Lincoln, Richard,Zong, Ruifa,Thummel, Randolph P.,McFarland, Sherri A.
, p. 2889 - 2900 (2010)
Several mononuclear Ru(ll) dyads possessing 1, 10-phenanthrollne-appended pyrenylethynylene llgands were synthesized, characterized, and evaluated for their potential in photobiologlcal applications such as photodynamlc therapy (PDT). These complexes interact with DNA via intercalation and photocleave DNA in vitro at submlcromolar concentrations when irradiated with visible light (λirr ≥ 400 nm). Such properties are remarkably sensitive to the position of the ethynylpyrenyl substituent on the 1, 10-phenanthroline ring, with 3-substitutlon showing the strongest binding under all conditions and causing the most deleterious DNA damage. Both dyads photocleave DNA under hypoxic conditions, and this photoactlvity translates well to cytotoxicity and photocytotoxlcity models using human leukemia cells, where the 5- and 3-substituted dyads show photocytotoxiclty at 5-10μM and 10-20μM, respectively, with minimal, or essentially no, dark toxicity at these concentrations. This lack of dark cytotoxicity at concentrations where significant photoactlvity Is observed emphasizes that agents with strong intercalating units, previously thought to be too toxic for phototherapeutic applications, should not be excluded from the arsenal of potential photochemotherapeutic agents under investigation.
Phenanthroline-Based Molecular Switches for Prospective Chemical Grafting: A Synthetic Strategy and Its Application to Spin-Crossover Complexes
Heinemann, Frank W.,Khusniyarov, Marat M.,Lindner, Thomas,M?rtel, Max,Scheurer, Andreas
, p. 2659 - 2666 (2020)
1,10-Phenanthroline represents a well-known versatile ligand system finding many applications in chemistry, biology, and material science. The properties and thus the use of these molecules are determined by coordinating metal ions and ligand substituents. Advanced ligand systems that, for instance, feature simultaneously an integrated photochrome and a surface anchoring group require the introduction of several differing substituents and the synthesis of asymmetric derivatives. In spite of a long history of the ligand system - and to our great surprise - a general synthetic approach allowing the introduction of differing substituents at positions (3,8) and (5,6) of 1,10-phenanthroline is not known. Here, we present a general approach for the synthesis of such phenanthrolines. The approach is used to integrate a diarylethene photochrome into a functionalized phenanthroline and thus to synthesize a novel photoswitchable phenanthroline and a corresponding spin-crossover molecular photoswitch. The functionality of both the ligand and its iron(II) complex at room temperature has been demonstrated. The importance of this work for chemical grafting of molecular switches based on phenanthrolines is emphasized.
Facile synthesis and self-assembly of diazafluorenone-based p-n (donor-acceptor) organic semiconductors
Li, Wei-Jie,Wu, Hai-Mei,Li, Yi-Bao,Hu, Chao-Peng,Yi, Ming-Dong,Xie, Ling-Hai,Chen, Lin,Zhao, Jian-Feng,Zhao, Xiang-Hua,Shi, Nai-En,Qian, Yan,Wang, Chen,Wei, Wei,Huang, Wei
, p. 8216 - 8221 (2012)
A mild and effective method to prepare 2,7-dibromo-4,5-diazafluoren-9-one (3) has been described involving tandem oxidation and rearrangement reactions. Diazafluorenone-based donor-acceptor (p-n) molecules via stille coupling reactions exhibit solvent-dep
D-π-A dye sensitizers made of polymeric metal complexes containing 1,10-phenanthroline and alkylfluorene or alkoxybenzene: Synthesis, characterization and photovoltaic performance for dye-sensitized solar cells
Yu, Xiaoguang,Jin, Xueliang,Tang, Guipeng,Zhou, Jun,Zhang, Wei,Peng, Dahai,Hu, Jiaomei,Zhong, Chaofan
, p. 5893 - 5901 (2013)
Four polymeric metal complexes (P1-P4 based on 1,10-phenanthroline metal complexes and alkylfluorene or alkoxybenzene were synthesized by the Heck coupling reaction and were developed for dye-sensitized solar cell applications. The target dyes use alkoxyb
Synthesis and luminescent properties of novel silicon-based electroluminescent copolymers with ruthenium(II)-chelated complexes
Baek, Nam Seob,Kim, Hwan Kyu,Hwang, Gil Tae,Kim, Byeang Hyean
, p. 387 - 390 (2001)
A new class of silicon-based alternating copolymers having Ruthenium(II)-chelated complexes was synthesized to use as electroluminescent materials by Heck reaction between organosilicon divinyl monomers and Ru(II)-chelated monomers. The incorporation of o
Novel donor-acceptor type thiophene pyridine conjugates: Synthesis and ion recognition features
Algi, Fatih
, p. 3523 - 3529 (2013)
In order to reveal the effect of the donor units on the structure-property relationship, three novel directly linked donor-acceptor type systems, 1-3, which are based on thiophene and pyridine conjugates, are designed, synthesized and characterized by spe
Simple One-Step Synthesis of 3-Bromo- and 3,8-Dibromo-1,10-Phenanthroline: Fundamental Building Blocks in the Design of Metal Chelates
Tzalis, Dimitrios,Tor, Yitzhak,Failla, Salvatorre,Siegel, Jay S.
, p. 3489 - 3490 (1995)
Commercially available 1,10-phenanthroline monohydrochloride monohydrate (1) reacts with bromine to give 3-bromo-1,10-phenanthroline (2) and 3,8-dibromo-1,10-phenanthroline (3) as major products in a one step reaction.
A highly efficient red-emitting ruthenium complex with 3,5-difluorophenyl substituents
Zhu, Yingying,Fei, Teng,Ma, Yuguang
, p. 73 - 79 (2016)
Five 3,5-difluorophenyl-substituted ruthenium complexes [Ru(bpy)2(dfpbpy)(ClO4)2] (Ru-Fbpy-bpy; bpy=bipyridine, dfpbpy=5,5′-di(3,5-difluorophenyl)-2,2′-bipyridine), [Ru(dpp)2(dfpbpy)(ClO4)2] (Ru-Fbpy-dpp; dpp=4,7-diphenyl-1,10-phenanthroline), [Ru(dpp)2(dfpphen)(ClO4)2] (Ru-Fphen-dpp; dfpphen=5,5′-di(3,5-difluorophenyl)-1,10-phenanthroline), [Ru(dpp)2(4,7-dfpphen)(ClO4)2] (Ru-Fdpp-dpp; 4,7-dfpphen=4,7-di(3,5-difluorophenyl)-1,10-phenanthroline), and [Ru(4,7-dfpphen)3(AsF6)2] (Ru-Fdpp) were synthesized, and their photophysical, electrochemical, and electroluminescent properties were studied systematically. The introduction of the electron-withdrawing group 3,5-difluorophenyl leads to a redshift of the emission of the ruthenium complexes. In addition, the 3,5-difluorophenyl substituent extends the π conjugation of the ligand, and thus facilitates the metal-to-ligand charge-transfer process of the complexes. All the complexes display orange-red phosphorescent emissions centered at 638, 638, 624, 614, and 605 nm, respectively. Density functional theory calculations show that the lowest unoccupied molecular orbital of Ru-Fbpy-dpp, Ru-Fphen-dpp, and Ru-Fdpp-dpp are all distributed on the 3,5-difluorophenyl-substituted ligand. By using these complexes as emitters, highly luminescent single-layer devices are obtained. The optimized device based on Ru-Fdpp exhibits the highest luminous efficiency and power efficiency of 4.19 cd A-1 and 1.46 lm W-1, respectively. Bright ideas: Five 3,5-difluorophenyl-substituted ruthenium complexes have been synthesized and characterized. The photoluminescent efficiencies of the complexes improved after introduction of an electron-withdrawing substituent (see scheme). The complexes are suitable as dopant light-emitting materials for organic light-emitting diodes.
Preparation and properties of ?-conjugated poly(1,10-phenanthroline-3,8-diyl)
Saitoh, Yutaka,Yamamoto, Takakazu
, p. 785 - 786 (1995)
Poly(1,10-phenanthroline-3,8-diyl) has been synthesized by dehalogenation polycondensation of 3,8-dibromo-1,10-phenanthroline with a zerovalent nickel complex.The polymer has molecular weihgt of 6800 and is electrochemically reduced at Epa=2.24
