Phosphorescent Pt(ii) complexes bearing a monoanionic C^N^N luminophore and tunable ancillary ligands

2017 ◽  
Vol 46 (10) ◽  
pp. 3160-3169 ◽  
Author(s):  
Marian Hebenbrock ◽  
Linda Stegemann ◽  
Jutta Kösters ◽  
Nikos L. Doltsinis ◽  
Jens Müller ◽  
...  
Keyword(s):  
Excited State ◽  
Click Chemistry ◽  
Intermolecular Interactions ◽  
Triazole Ring ◽  
Ancillary Ligands

A new monoanionic pincer luminophore is presented, yielding phosphorescent Pt(ii) complexes bearing a neutral 1,2,3-triazole ring introduced via click chemistry. The overall charge, intermolecular interactions and excited state properties can be manipulated and controlled.

scholarly journals 4-[(E)-(4-Hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione

2014 ◽  
Vol 70 (6) ◽  
pp. o733-o734 ◽  
Author(s):  
Balladka K. Sarojini ◽  
Padmanabha S. Manjula ◽  
B. Narayana ◽  
Jerry P. Jasinski
Keyword(s):  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Hydroxy Group ◽  
Title Compound ◽  
Triazole Ring ◽  
Compound C ◽  
Centroid Distance ◽  
Group Form ◽  
The Mean ◽  
Graph Set

The title compound, C10H10N4OS, is nearly planar with the mean planes of the hydroxybenzyl and triazole rings inclined at an angle of only 3.2 (7)°. In the crystal, O—H...N hydrogen bonds between the hydroxy group and the triazole ring in concert with weak N—H...S intermolecular interactions between the triazole ring and thione group form chains along [-210] enclosingR22(8) graph-set motifs. A weak intramolecular C—H...S interaction and intermolecular π–π interactions [centroid–centroid distance = 3.5990 (15) Å] are also observed.

Role of Intermolecular Interactions in the Excited-State Photophysics of Tetracene and 2,2′-Ditetracene

2020 ◽  
Vol 124 (36) ◽  
pp. 19435-19446 ◽  
Author(s):  
Ulrich Müller ◽  
Lena Roos ◽  
Maximilian Frank ◽  
Marian Deutsch ◽  
Sebastian Hammer ◽  
...  
Keyword(s):  
Excited State ◽  
Intermolecular Interactions

Synthetic Control of Excited-State Properties in Cyclometalated Ir(III) Complexes Using Ancillary Ligands

2005 ◽  
Vol 44 (6) ◽  
pp. 1713-1727 ◽  
Author(s):  
Jian Li ◽  
Peter I. Djurovich ◽  
Bert D. Alleyne ◽  
Muhammed Yousufuddin ◽  
Nam N. Ho ◽  
...  
Keyword(s):  
Excited State ◽  
Synthetic Control ◽  
Ancillary Ligands

Exciton-photon coupling in molecular crystals

1966 ◽  
Vol 292 (1428) ◽  
pp. 78-91 ◽  
Keyword(s):  
Excited State ◽  
Intermolecular Interactions ◽  
Energy Levels ◽  
Molecular Crystals ◽  
Electronic States ◽  
Dipole Approximation ◽  
Electronic Charge ◽  
Exciton Energy ◽  
Molecular Excitons ◽  
Photon Coupling

The theory of Frenkel molecular excitons is extended to include the effect of retardation , in the dipole approximation, on the mixing of exciton bands arising from different electronic states. The Hamiltonian does not contain any instantaneous intermolecular interactions and treats exciton-photon and intermolecular interactions on an equal footing. The exciton energy levels are calculated to the fourth order in electronic charge using graphs of the time-ordered type and it is shown that retardation results in a replacement of instantaneous dipole potentials by retarded resonance potentials. A number of results for a system of three identical molecules with one in an excited state are calculated simultaneously.

Competition and Interplay of Various Intermolecular Interactions in Ultrafast Excited-State Proton and Electron Transfer Reactions

2014 ◽  
Vol 119 (6) ◽  
pp. 2444-2453 ◽  
Author(s):  
Michael G. Kuzmin ◽  
Irina V. Soboleva ◽  
Vladimir L. Ivanov ◽  
Elizabeth-Ann Gould ◽  
Dan Huppert ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Excited State ◽  
Intermolecular Interactions ◽  
Transfer Reactions ◽  
Electron Transfer Reactions

scholarly journals SYNTHESIS OF A 1,2,3-TRIAZOLE-CONTAINING MACROCYCLE BASED ON THE "CLICK CHEMISTRY" REACTION AND ANALYSIS OF ITS PLANAR CHIRALITY USING NMR AND DFT CALCULATIONS

2020 ◽  
pp. 55-61
Author(s):  
H. Yampolska ◽  
S. Kharchenko ◽  
A. Kozytskyi ◽  
A. Kyrylchuk ◽  
Z. Voitenko ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Click Chemistry ◽  
Protein Interactions ◽  
Variable Temperature ◽  
Triazole Ring ◽  
Building Blocks ◽  
Ring Closure ◽  
Amide Bond ◽  
High Yield ◽  
Planar Chirality

Macrocycles represent previously unexplored promising drug candidates, that can be useful for treating protein-protein interactions. Atropoisomerism is an inherent feature of the natural macrocyclic peptides that is significant for their activity and selectivity, and, therefore, should be introduced into newly synthesized macrocycles. Synthesis of the libraries of artificial macrocycles faces many challenges due to their structure and size. Herein we report on the preparation of a 16-membered macrocycle containing 1,2,3-triazole ring, spiro-piperidine, and phenyl moieties, as well as a chiral carbon atom. Our approach to the macrocycle was inspired by the "build/couple/pair" (B/C/P) strategy, a part of diversity-oriented synthesis methodology. We have employed readily accessible starting materials and robust synthetic procedures which allowed us to obtain the target macrocycle in a high yield. Standard methods of amide bond formation were used for the coupling of macrocycle building blocks. Click chemistry azide-alkyne cycloaddition was exploited at the final ring closure step. The assignment of signals in 1H and 13C NMR spectra of the macrocycle was performed using a series of 2D NMR techniques. The macrocycle displayed planar chirality, which, in a combination with a stereocenter with the known configuration, was sufficient to propose possible structures of diastereomers. The diastereomers could differ by the relative position of triazole ring. Their racemization could occur through a "rope skipping" motion involving the cyclic chain crossing the plane of 1,2,3-triazole ring. The supposed structures of diastereomers were corroborated by means of a various NMR spectroscopy techniques and DFT calculations. Analysis of the amide NH chemical shift temperature coefficients coupled with the data on optimized geometries obtained by DFT convincingly demonstrated that the intramolecular hydrogen bonds play a major role in stabilization of the diastereomer structures. According to the variable temperature NMR experiment, the interconversion of two diastereomers did not occur even at heating up to 70 °C.

scholarly journals Occurrence of excited state charge separation in a N-doped graphene–perylenediimide hybrid formed via ‘click’ chemistry

2019 ◽  
Vol 1 (10) ◽  
pp. 4009-4015 ◽  
Author(s):  
Habtom B. Gobeze ◽  
Luis M. Arellano ◽  
Ana María Gutiérrez-Vílchez ◽  
María J. Gómez-Escalonilla ◽  
Ángela Sastre-Santos ◽  
...  
Keyword(s):  
Excited State ◽  
Click Chemistry ◽  
Charge Separation ◽  
Perylene Diimide ◽  
Doped Graphene ◽  
Donor Acceptor ◽  
State Charge

A donor–acceptor hybrid was devised and synthesized using N-doped graphene and perylene diimide via click chemistry, and the occurrence of excited state charge separation is demonstrated.

scholarly journals Microwave-Assisted Synthesis of Novel Bis-Flavone Dimers as New Anticancer Agents

2018 ◽  
Vol 16 (1) ◽  
pp. 66-75 ◽  
Author(s):  
Andrew McGown ◽  
Abby Ragazzon-Smith ◽  
John A. Hadfield ◽  
Herman Potgetier ◽  
Patricia A. Ragazzon
Keyword(s):  
Anticancer Activity ◽  
Click Chemistry ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Triazole Ring ◽  
Microwave Assisted Synthesis ◽  
Anticancer Properties ◽  
Microwave Assisted ◽  
Ic50 Values ◽  
High Yields

In this study, we describe a microwave-based click chemistry method used to prepare a family of novel bis-flavone dimers. The substituted 7-hydroxy and 4’-hydroxy flavonoids were linked through a triazole ring. The compounds were easily synthesized and purified in high yields. The bisflavonoids were tested on different cell lines including HCT116, HepG2, MCF7 and MOLT-4. Several analogues showed to have anticancer activity with IC50 values in the range of 20-60 μM. Flavonoids are known for their anticancer properties and this method provides the basis for new medicinal structures.

β-Diketiminate-Supported Iridium Photosensitizers with Increased Excited-State Reducing Power

2021 ◽  
Author(s):  
Jong-Hwa Shon ◽  
Dooyoung Kim ◽  
Thomas G Gray ◽  
Thomas S. Teets
Keyword(s):  
Excited State ◽  
Reducing Power ◽  
Iridium Complexes ◽  
Ancillary Ligands

A series of bis-cyclometalated iridium complexes were prepared which combine triazole or NHC-based cyclometalating ligands with substituted β-diketiminate (NacNac) ancillary ligands. The HOMO is localized on the NacNac ligand and...

Using Sodium Hydride and Potassium Carbonate as Bases in Synthesis of Substituted 2-Amino-4-aryl-7-propargyloxy-4H-chromene-3-carbonitriles

2019 ◽  
Vol 16 (3) ◽  
pp. 423-430
Author(s):  
Nguyen D. Thanh ◽  
Do S. Hai ◽  
Vu T.N. Bich ◽  
Pham T.T. Hien ◽  
Nguyen T.K. Duyen ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Potassium Carbonate ◽  
Sodium Hydride ◽  
Triazole Ring ◽  
Biological Properties ◽  
Alkylation Reaction ◽  
Propargyl Bromide ◽  
Propargyl Ether ◽  
Ether Synthesis ◽  
Chromene Ring

Aims and Objective: 1-Alkynes are the important precursors for the CuAAC click chemistry. The hybrid of 1,2,3-triazole ring to the chromene ring and sugar moiety could bring some remarkable biological properties. Propargyl derivatives are usually used in the click chemistry. This article reported the synthesis of 2-amino-4-aryl-7-propargyloxy-4-aryl-4H-chromene-3-carbonitriles using propargyl bromide as alkylation agent and the use of potassium carbonate and sodium hydride as bases in the conversion of 2-amino-4-aryl-7- hydroxy-4-aryl-4H-chromene-3-carbonitriles into corresponding propargyl ethers in Williamson’s ether synthesis. Materials and Methods: The use of CTAB for the synthesis of benzylidene malononitriles and anhydrous potassium carbonate as a catalyst in absolute ethanol in the synthesis of 2-amino-7-hydroxy-4H-chromene-3- carbonitriles is an efficient and simple synthetic method. Propargyl ether compounds of these 4H-chromene-3- carbonitriles were obtained from the alkylation reaction by propargyl bromide. Two procedures were applied: K2CO3 as a base in acetone solvent (Procedure A) and NaH as a base in DMF solvent (Procedure B). The single-crystal X-ray structure of propargyl ether 5e has been studied. Results: The use of K2CO3 and NaH as bases in the Williamson’s ether synthesis from 2-amino-7-hydroxy-4Hchromene- 3-carbonitriles showed that Procedure B was the better route and gave ethers in the higher yields. 2- Amino-4-aryl-7-propargyloxy-4-aryl-4H-chromene-3-carbonitriles were obtained from corresponding 7- hydroxy-4H-chromene-3-carbonitriles. Yields of ethers 5a-i were 70−89% and 80−96%, respectively depending on the used procedures. Conclusion: The described methods are simple, clean and environmentally friendly alternatives for the preparation of 2-amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles. The conditions for the transformation of these compounds into propargyl ethers include dried DMF as a solvent, NaH as a base and reaction time of 2 h at the room temperature. A series of 2-amino-4-aryl-7-hydroxy-4-aryl-4H-chromene-3-carbonitriles were obtained based on investigated reaction condition.

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