Synthesis, characterisation, electrochemical study and photovoltaic measurements of a new terpyridine and pyridine-quinoline based mixed chelate ruthenium dye

Mongal, Binitendra Naath; Pal, Arunava; Mandal, Tarun K.; Datta, Jayati; Naskar, Subhendu

doi:10.1016/j.poly.2015.10.040

Cited by 14 publications

(6 citation statements)

References 57 publications

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“…This also means that purines with low p K a values should be better candidates to act as copper chelating agents. In addition, it has been reported that purines, and other ligands, lower their p K a s when bound to metals . This particular feature was also tested here.…”

Section: Resultsmentioning

confidence: 77%

Role of purines on the copper‐catalyzed oxidative damage in biological systems: Protection versus promotion

Castañeda‐Arriaga

Pérez-González

Álvarez-Idaboy

et al. 2017

Int J of Quantum Chemistry

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Oxidative damage to biomolecules is a serious health-threatening issue, which leads to the development of several diseases. Oxidative conditions are frequently catalyzed by metal ions. In this study, the role of purines in the copper-catalyzed oxidative stress was investigated using the density functional theory. The obtained results indicate that purines can have a dual behavior, acting as both protectors and promoters of oxidative stress. Their protection role arises from their known radical scavenging activity, as well as their ability to chelate Cu(II) leading to complexes that areto some extent-harder to reduce than free Cu(II). Conversely, their pro-oxidant role is a consequence of their reductant behavior, when deprotonated. Thus, the purines' anions can reduce Cu (II) to Cu(I), making the latter available to be involved in Fenton-like reactions. Consequently, mixtures of purines and Cu(II), at pHs where the fraction of deprotonated purines is rather significant, would yield • OH radicals. In turn, these very reactive radicals would damage biological targets such as lipids, proteins, and DNA.antioxidants, kinetics, pro-oxidants, rate constants, reaction mechanism 1 | I N TR ODU C TI ON Oxidative damage (OD) to biological targets such as lipids, proteins, and DNA is a serious health-threatening phenomenon. It has been held responsible, at least in part, for the onset and development of several diseases including cancer [1][2][3] ; rheumatoid arthritis [4][5][6] ; neurodegenerative disorders such as Parkinson's and Alzheimer's diseases, depression, multiple sclerosis, and memory loss [7][8][9][10][11][12][13] ; cardiovascular diseases such as atherosclerosis, ischemia, hypertension, cardiac hypertrophy, heart failure, and cardiomyopathy [14][15][16][17] ; as well as renal [18][19][20] and pulmonary failure. [21][22][23] OD arises as a consequence of a chemical imbalance between the production and consumption of oxidants, known as oxidative stress (OS). [24] One of the most damaging oxidants in biological systems is the hydroxyl radical ( • OH). It can be produced, in the presence of metal ions such as Fe(II) or Cu(I), by Fenton or Fenton-like reactions (M q 1 H 2 O 2 ! M q11 1OH -1 • OH). However, the most stable and abundant forms of these two metals, under physiological conditions, are Fe(III) and Cu(II). Thus, • OH production would actually involve the metal-catalyzed Haber-Weiss recombination (HWR). It comprises two chemical steps. The first one is the reduction of the metal ions (M q11 1 O •2 2 ! M q 1 3 O 2 ) and the second one is the Fenton reaction. Consequently, redox active metal ions are of particular interest for the chemistry of living systems. These ions cannot only bind to DNA, but they can also promote OD to DNA by mediating the production of oxygen reactive species (ROS). [25] In fact metal-mediated OD to DNA has become an important topic in metal toxicity and carcinogenesis. [26][27][28][29]

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Section: Resultsmentioning

confidence: 77%

Role of purines on the copper‐catalyzed oxidative damage in biological systems: Protection versus promotion

Castañeda‐Arriaga

Pérez-González

Álvarez-Idaboy

et al. 2017

Int J of Quantum Chemistry

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“…Fundamental and extensive understanding of the binding properties and the energetic of the copper‐artificial amino acid complexes were reported, and apparently, there is no doubt about the conformations that authors proposed in that theoretical study as the most likely ones. However, it was not considered the most abundant species of DPEN at physiological conditions; planar structures were not investigated neither mono‐dentate compounds; and only the direct chelation mechanism (DCM) was considered, although there are experiments indicating that the coupled‐deprotonation‐chelation mechanism (CDCM) is a more likely route, that is, the p K a s of ligands lower when bound to the metal . In the particular case of DPEN it has been reported that its second and third p K a s decrease as a consequence of the interaction with metals …”

Section: Introductionmentioning

confidence: 99%

How to identify promising metal scavengers? d‐penicillamine with copper as a study case

Martı́nez

Vargas

Galano

2017

Int J of Quantum Chemistry

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Therapeutic chelating agents are used to prevent the effects of the metal accumulation. These are molecules that form complexes with transition metals and they are referred here as metal scavengers. The main idea of this investigation is to recognize the most relevant chemical features to identify potential metal scavengers. D-penicillamine with copper (DPEN-Cu) is used for this purpose. The first requirement that must be fulfilled by a good metal scavenger is the exergonicity of the chelating reaction. In the DPEN-Cu case the most likely complexation pathway was found to have DG equal to 224.3 kcal/mol. It is desirable that the chelating molecule could also be a free radical scavenger. D-penicillamine is a good free radical scavenger following the hydrogen atom transfer reaction. An additional advantage is that the DPEN-Cu may act as ·OH-inactivating ligand.It is proposed that chelating agents fulfilling these requirements may be a promising candidate to be used in metal chelation therapies as metal scavengers. K E Y W O R D S antioxidant, antiradical, chelating therapy, scavenger Int J Quantum Chem. 2018;118:e25457.

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“…In this case, a further enhancement in π-conjugation led to increased molar extinction coefficients and improved performances. Similar complexes that bear donating groups on the terpyridine and electron withdrawing/grafting moieties on a bidentate ligand have been proposed by Mosurkal [103], Erten-Ela [104] and, more recently, by Mongal [105]. In the first case, the anchoring moiety was provided by 4,4’-dicarboxy-2,2’-bipyridine.…”

Section: Modifications Of Black Dye and Structure-properties Relatmentioning

confidence: 62%

Terpyridine and Quaterpyridine Complexes as Sensitizers for Photovoltaic Applications

et al. 2016

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Terpyridine and quaterpyridine-based complexes allow wide light harvesting of the solar spectrum. Terpyridines, with respect to bipyridines, allow for achieving metal-complexes with lower band gaps in the metal-to-ligand transition (MLCT), thus providing a better absorption at lower energy wavelengths resulting in an enhancement of the solar light-harvesting ability. Despite the wider absorption of the first tricarboxylate terpyridyl ligand-based complex, Black Dye (BD), dye-sensitized solar cell (DSC) performances are lower if compared with N719 or other optimized bipyridine-based complexes. To further improve BD performances several modifications have been carried out in recent years affecting each component of the complexes: terpyridines have been replaced by quaterpyridines; other metals were used instead of ruthenium, and thiocyanates have been replaced by different pinchers in order to achieve cyclometalated or heteroleptic complexes. The review provides a summary on design strategies, main synthetic routes, optical and photovoltaic properties of terpyridine and quaterpyridine ligands applied to photovoltaic, and focuses on n-type DSCs.

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Synthesis, characterisation, electrochemical study and photovoltaic measurements of a new terpyridine and pyridine-quinoline based mixed chelate ruthenium dye

Cited by 14 publications

References 57 publications

Role of purines on the copper‐catalyzed oxidative damage in biological systems: Protection versus promotion

Role of purines on the copper‐catalyzed oxidative damage in biological systems: Protection versus promotion

How to identify promising metal scavengers? d‐penicillamine with copper as a study case

Terpyridine and Quaterpyridine Complexes as Sensitizers for Photovoltaic Applications

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