Unravelling the miniscule size effect of auxiliary donor in D-D-π-A type dipolar photosensitizers on quasi-solid state DSSC performance

Kumar, Chitra; Raheem, Abbasriyaludeen Abdul; Ramesh, Mohan; Shanmugam, Ramasamy; Praveen, Chandrasekar

doi:10.1016/j.dyepig.2020.108959

Cited by 16 publications

(11 citation statements)

References 38 publications

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“…n -Alkylation of 3 with 1-bromohexane using NaH as the base produces the required carbazole precursor 4 in excellent yield. The preparation of the other starting material, 2,7-dibromo-9,9-dioctyl-9 H -fluorene 7 , commenced from the FeBr 3 -catalyzed Friedel–Crafts bromination of fluorene 5 , forming dibromofluorene 6 . A double alkylation of 6 with 1-bromooctane under basic conditions affords the synthon 7 .…”

Section: Resultsmentioning

confidence: 99%

“…The preparation of the other starting material, 2,7-dibromo-9,9-dioctyl-9H-fluorene 7, commenced from the FeBr 3 -catalyzed Friedel−Crafts bromination of fluorene 5, forming dibromofluorene 6. 13 A double alkylation of 6 with 1-bromooctane under basic conditions affords the synthon 7. Notably, single crystals of 6 and 7 were isolated by evaporating the respective worked-up solution under atmospheric conditions (Tables S1 and S2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…However, undertaking this challenge requires methodical insight on the structure-guided property relationship of the targeted acceptor. As part of our endeavor on π-semiconductors, − we undertook this consideration by integrating a strong electron-withdrawing group on the A–D–A-type molecular backbone to derive fine-tuned optoelectronic and physicochemical properties to establish alternative n-type acceptors. In particular, our emphasis was to incorporate tetracyanobutadiene (TCBD) as a peripheral group to diminish the π-orbital energy in order to fulfill the acceptor criteria.…”

Section: Introductionmentioning

confidence: 99%

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Calamitic-Type Dipolar and Quadrupolar Chromophores with a Twisted Peripheral Handle: Structure–Property Outlook as Nonfullerene Acceptors for Binary Solar Cells

Raheem

Kumar

Murugan

et al. 2021

ACS Appl. Energy Mater.

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Symmetrical (14, 15) and unsymmetrical (16, 17) molecules possessing tetracyanobutadiene (TCBD) as a twisted end group on the carbazole/fluorene backbone were synthesized as nonfullerene acceptors (NFAs). Systematic structural correlation of these chromophores on the optoelectronic, electrochemical, and physicochemical properties revealed better acceptor properties for symmetrical (14, 15) compared to unsymmetrical analogues (16, 17). High molar absorptivity, deep HOMO–LUMOs, better electron-accepting capacity, along with other complementary molecular properties are some of the associated factors for the better acceptor character. In a binary solar cell configuration blended with P3HT donor, quadrupolar-type symmetrical chromophores (14, 15) displayed higher power conversion efficiencies over dipolar-type unsymmetrical chromophores (16, 17). In particular, 14 with an efficiency of 5.37% emerged as the best candidate with further enhancement to 6.30% upon additive processing. The dependence of processing on the improved photoinduced current was attributed to the better nanoscale morphology, crystallinity, and electron mobility. In terms of efficiency, it is the third highest for any TCBD-based NFA solar cells. Overall, this work validates the impact of a nonplanar TCBD auxiliary positioned within a calamitic-type π-framework to realize alternative NFAs. Viewed from a fundamental perspective, the initial results are promising, and further fine tuning of the molecular structure could possibly form an ideal acceptor for organic photovoltaics.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Calamitic-Type Dipolar and Quadrupolar Chromophores with a Twisted Peripheral Handle: Structure–Property Outlook as Nonfullerene Acceptors for Binary Solar Cells

Raheem

Kumar

Murugan

et al. 2021

ACS Appl. Energy Mater.

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“…Generally, the atoms with a higher f k + are more likely to accept an electron from the metal surface, while those with a greater f k À are more likely to donate an electron to the iron surface. [88][89][90] The analysis of the Fukui indices shows that both NTM profiles, neutral and protonated, have several active donor-acceptor sites, which can promote the adsorption of these states on the metal surface. These results indicate that the C(12) and C( 16) sites on the neutral form have high values of f k + .…”

Section: Location Of Active Centersmentioning

confidence: 99%

Systematic investigation of the adsorption and inhibition properties of a new clickable 1,2,3‐triazole compound for mild steel in 1 M HCl medium

et al. 2021

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The search for eco‐friendly and effective corrosion inhibitors for the acidizing processes is increasingly required. In the present study, a new 1,2,3‐triazole derivative, namely, 4‐(1‐naphthalen‐2‐ylmethyl‐1H‐[1,2,3]triazol‐4‐ylmethyl)‐morpholine (NTM), has been clicked under green click synthesis conditions and fully characterized. The inhibition performance on corroded mild steel (MS) was studied by electrochemical impedance spectroscopy (EIS), potentiodynamic polarization (PDP) and weight loss measurements. The electrochemical results indicate that NTM works as a mixed‐type inhibitor and its adsorption on the MS surface obeys the Langmuir adsorption isotherm. The corrosion process was found to be reduced at 10−3 M concentration with 94 % efficiency. An immersion time of 57.56 min using a concentration of NTM equal to 5.2×10−4 M at 298 K was selected as optimal inhibition process conditions through the Central Composite Design (CCD). These conditions were conducted to the desirability of 1.00 and 88.8 % as the expected inhibition. NTM species was adsorbed on the MS surface by physical and chemical interactions. Quantum chemical calculations performed at the DFT/6‐31G(d,p) and DFTB+ levels were used to examine the adsorption of neutral NTM and its protonated form on the MS surface, including the active centers of both species. The mode of orientations of neutral and protonated NTM on the MS surface and the corresponding adsorption energies in both gas and aqueous phases were explored by molecular simulation dynamics.

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“…To this end, the present review sum up the regioselective heterocyclization by activation of π‐functionality tethered nucleophiles under the catalytic action of gold. With my journey on various aspects of heterocyclics ranging from methodology [106–112] to medicinal chemistry [113–125] and sustainable energy, [126–133] the present review is particularly intended to cover only heterocyclization. Depending on the substrate class based on the nature of heteroatom and π‐residue, this review is categorized into various sub‐sections with ample illustrations.…”

Section: Introductionmentioning

confidence: 99%

Cycloisomerization of π‐Coupled Heteroatom Nucleophiles by Gold Catalysis: En Route to Regiochemically Defined Heterocycles

Praveen

2021

The Chemical Record

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Since the dawn of millennium, catalytic gold chemistry is at the forefront to set off diverse organic reactions via unique activation of π‐bonded molecules. Within this purview, cycloisomerization of heteroatom nucleophiles linked to a π‐system is one of the well recognized chemistry for the construction of numerous heterocyclic cores. Though the rudimentary aspects of this transformation are reviewed by several groups in different timeline, a holistic view on regiochemistry of such reactions went largely overlooked. Hence, this account emphasizes the gold catalyzed regioselective cycloisomerization of structurally distinctive π‐connected hetero‐nucleophiles leading to different heterocycles documented in the last two decades. From an application perspective, this account also highlights those methodologies which find a role in the total synthesis of natural products. Wherever appropriate, mechanistic details and contributing factors for selectivity are also discussed.

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Unravelling the miniscule size effect of auxiliary donor in D-D-π-A type dipolar photosensitizers on quasi-solid state DSSC performance

Cited by 16 publications

References 38 publications

Calamitic-Type Dipolar and Quadrupolar Chromophores with a Twisted Peripheral Handle: Structure–Property Outlook as Nonfullerene Acceptors for Binary Solar Cells

Calamitic-Type Dipolar and Quadrupolar Chromophores with a Twisted Peripheral Handle: Structure–Property Outlook as Nonfullerene Acceptors for Binary Solar Cells

Systematic investigation of the adsorption and inhibition properties of a new clickable 1,2,3‐triazole compound for mild steel in 1 M HCl medium

Cycloisomerization of π‐Coupled Heteroatom Nucleophiles by Gold Catalysis: En Route to Regiochemically Defined Heterocycles

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