Literature DB >> 27355786

Effects of Methyl Substitution in Ruthenium Tris(2-pyridylmethyl)amine Photocaging Groups for Nitriles.

Karan Arora1, Jessica K White2, Rajgopal Sharma1, Shivnath Mazumder1, Philip D Martin1, H Bernhard Schlegel1, Claudia Turro2, Jeremy J Kodanko1,3.   

Abstract

Four complexes of the general formula class="Chemical">[Ru(L)(CH3CN)2](PF6)2, [L = n class="Chemical">TPA (5), MeTPA (6), Me2TPA (7), and Me3TPA (8)] [TPA = tris[(pyridin-2-yl)methyl]amine, where methyl groups were introduced consecutively onto the 6-position of py donors of TPA, were prepared and characterized by various spectroscopic techniques and mass spectrometry. While 5 and 8 were isolated as single stereoisomers, 6 and 7 were isolated as mixtures of stereoisomers in 2:1 and 1.5:1 ratios, respectively. Steric effects on ground state stability and thermal and photochemical reactivities were studied for all four complexes using (1)H NMR and electronic absorption spectroscopies and computational studies. These studies confirmed that the addition of steric bulk accelerates photochemical and thermal nitrile release.

Entities:  

Year:  2016        PMID: 27355786      PMCID: PMC4966558          DOI: 10.1021/acs.inorgchem.6b00650

Source DB:  PubMed          Journal:  Inorg Chem        ISSN: 0020-1669            Impact factor:   5.165


  58 in total

1.  Synthesis, spectroscopic characterization, photochemical and photophysical properties and biological activities of ruthenium complexes with mono- and bi-dentate histamine ligand.

Authors:  Carolina R Cardoso; Inara de Aguiar; Mariana R Camilo; Márcia V S Lima; Amando S Ito; Maurício S Baptista; Christiane Pavani; Tiago Venâncio; Rose M Carlos
Journal:  Dalton Trans       Date:  2012-04-26       Impact factor: 4.390

2.  N-acetylmethionine and biotin as photocleavable protective groups for ruthenium polypyridyl complexes.

Authors:  Roosmarijn E Goldbach; Isabel Rodriguez-Garcia; Joop H van Lenthe; Maxime A Siegler; Sylvestre Bonnet
Journal:  Chemistry       Date:  2011-07-27       Impact factor: 5.236

Review 3.  Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

Authors:  Petr Klán; Tomáš Šolomek; Christian G Bochet; Aurélien Blanc; Richard Givens; Marina Rubina; Vladimir Popik; Alexey Kostikov; Jakob Wirz
Journal:  Chem Rev       Date:  2012-12-21       Impact factor: 60.622

Review 4.  Light-controlled tools.

Authors:  Clara Brieke; Falk Rohrbach; Alexander Gottschalk; Günter Mayer; Alexander Heckel
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-24       Impact factor: 15.336

5.  Photochemical activation of ruthenium(II)-pyridylamine complexes having a pyridine-N-oxide pendant toward oxygenation of organic substrates.

Authors:  Takahiko Kojima; Kazuya Nakayama; Miyuki Sakaguchi; Takashi Ogura; Kei Ohkubo; Shunichi Fukuzumi
Journal:  J Am Chem Soc       Date:  2011-10-13       Impact factor: 15.419

6.  Photochemical expulsion of the neutral monodentate ligand L in Ru(terpy*)(diimine)(L)2+: a dramatic effect of the steric properties of the spectator diimine ligand.

Authors:  Sylvestre Bonnet; Jean-Paul Collin; Jean-Pierre Sauvage; Emma Schofield
Journal:  Inorg Chem       Date:  2004-12-27       Impact factor: 5.165

7.  Solid-phase synthesis as a platform for the discovery of new ruthenium complexes for efficient release of photocaged ligands with visible light.

Authors:  Rajgopal Sharma; Jessica D Knoll; Nicholas Ancona; Phillip D Martin; Claudia Turro; Jeremy J Kodanko
Journal:  Inorg Chem       Date:  2015-01-22       Impact factor: 5.165

8.  Selective Release of Aromatic Heterocycles from Ruthenium Tris(2-pyridylmethyl)amine with Visible Light.

Authors:  Ao Li; Jessica K White; Karan Arora; Mackenzie K Herroon; Philip D Martin; H Bernhard Schlegel; Izabela Podgorski; Claudia Turro; Jeremy J Kodanko
Journal:  Inorg Chem       Date:  2015-12-15       Impact factor: 5.165

9.  A [4+2] mixed ligand approach to ruthenium DNA metallointercalators [Ru(tpa)(N-N)](PF(6))(2) using a tris(2-pyridylmethyl)amine (tpa) capping ligand.

Authors:  Sabine Seeberg née Kraft; Caroline Bischof; Annette Loos; Sebastian Braun; Nigar Jafarova; Ulrich Schatzschneider
Journal:  J Inorg Biochem       Date:  2009-05-24       Impact factor: 4.155

10.  Unusually efficient pyridine photodissociation from Ru(II) complexes with sterically bulky bidentate ancillary ligands.

Authors:  Jessica D Knoll; Bryan A Albani; Christopher B Durr; Claudia Turro
Journal:  J Phys Chem A       Date:  2014-07-25       Impact factor: 2.781

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  6 in total

1.  Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.

Authors:  Roy Weinstain; Tomáš Slanina; Dnyaneshwar Kand; Petr Klán
Journal:  Chem Rev       Date:  2020-10-30       Impact factor: 60.622

2.  Ru(ii) polypyridyl complexes as photocages for bioactive compounds containing nitriles and aromatic heterocycles.

Authors:  Ao Li; Claudia Turro; Jeremy J Kodanko
Journal:  Chem Commun (Camb)       Date:  2018-02-01       Impact factor: 6.222

3.  Ru(II) Polypyridyl Complexes Derived from Tetradentate Ancillary Ligands for Effective Photocaging.

Authors:  Ao Li; Claudia Turro; Jeremy J Kodanko
Journal:  Acc Chem Res       Date:  2018-06-05       Impact factor: 22.384

4.  Intraligand Excited States Turn a Ruthenium Oligothiophene Complex into a Light-Triggered Ubertoxin with Anticancer Effects in Extreme Hypoxia.

Authors:  John A Roque Iii; Houston D Cole; Patrick C Barrett; Liubov M Lifshits; Rachel O Hodges; Susy Kim; Gagan Deep; Antonio Francés-Monerris; Marta E Alberto; Colin G Cameron; Sherri A McFarland
Journal:  J Am Chem Soc       Date:  2022-04-28       Impact factor: 16.383

5.  Ru(ii) complexes with diazine ligands: electronic modulation of the coordinating group is key to the design of "dual action" photoactivated agents.

Authors:  Dmytro Havrylyuk; Megha Deshpande; Sean Parkin; Edith C Glazer
Journal:  Chem Commun (Camb)       Date:  2018-11-01       Impact factor: 6.222

6.  Singlet Oxygen Formation vs Photodissociation for Light-Responsive Protic Ruthenium Anticancer Compounds: The Oxygenated Substituent Determines Which Pathway Dominates.

Authors:  Fengrui Qu; Robert W Lamb; Colin G Cameron; Seungjo Park; Olaitan Oladipupo; Jessica L Gray; Yifei Xu; Houston D Cole; Marco Bonizzoni; Yonghyun Kim; Sherri A McFarland; Charles Edwin Webster; Elizabeth T Papish
Journal:  Inorg Chem       Date:  2021-02-03       Impact factor: 5.165

  6 in total

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