Effect of heteroatom (S/Se) juggling in donor–acceptor–donor (D–A–D) fused systems: synthesis and electrochemical polymerization

Ghosh, Sirina; Das, Sarasija; Kumar, Neha Rani; Agrawal, Abhijeet R.; Zade, Sanjio S.

doi:10.1039/c7nj02394d

Cited by 27 publications

(22 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…QY values were found to be 0.58, 0.57, and 0.44, for F 2 BT-F, T 2 BT-F, and S 2 BT-F, respectively. Monomer S 2 BT-F exhibited relatively lower QY compared to the other two monomers due to the quenching effect of heavier selenium atom [11,34,35]. In order to understand the effect of fluorine atom on QY, we have also measured the QYs of nonfluorinated and fully fluorinated analogues of T 2 BT-F, namely 4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (T 2 BT) and 5,6-difluoro-4,7-di(thiophen-2-yl)benzo [c][1,2,5]thiadiazole (T 2 BT-2F), respectively, which were synthesized in our previous works [27].…”

Section: Electrochemical and Optical Properties Of Monomersmentioning

confidence: 96%

“…Moreover, these materials' spectral and electronic properties can easily be controlled via structural design and modification of the polymeric backbone or pendant group appended to this backbone [6][7][8][9]. In this respect, by merging the electron-deficient units (acceptor, A) with the electron-rich ones (donor, D), the desired intrinsic properties can be incorporated into the polymer backbone [10,11]. Among various acceptor moieties, 2,1,3-benzothiadiazole (BT) is one of the most widely used building blocks in designing donor-acceptor type polymers due to its strong electron-withdrawing nature [12,13].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Effect of the donor units on the properties of fluorinated acceptor based systems

et al. 2021

View full text Add to dashboard Cite

A new series of monomers in the donor-acceptor-donor array, namely 5-fluoro-4,7-di(furan-2-yl)benzo [c][1,2,5] thiadiazole (F 2 BT-F), and 5-fluoro-4,7-di(selenophen-2-yl)benzo [c][1,2,5] thiadiazole (S 2 BT-F), bearing 5-fluorobenzo[c][1,2,5]-thiadiazole as the acceptor moiety and furan and selenophene as the electron donating groups was synthesized and polymerized electrochemically. To compare heteroatom effect, thiophene analogue of newly synthesized F 2 BT-F and S 2 BT-F namely, (5-fluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5] thiadiazole (T 2 BT-F)) and its corresponding polymer were also synthesized. Effect of donor units on the electrochemical and optical properties of fluorinated acceptor based systems was investigated in terms of the effect of different sized heteroatoms in five-membered rings on the dihedral angle and planarity. Theoretical calculations also suggested a deviation from planarity upon fluorination. Moreover, electrochemically obtained polymers possess low bandgap values (1.62 eV-1.68 eV for PF 2 BT-F and PS 2 BT-F, respectively) and exhibited electrochromic properties with relatively low switching times.

show abstract

Section: Electrochemical and Optical Properties Of Monomersmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Effect of the donor units on the properties of fluorinated acceptor based systems

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[ 17,18 ] We have recently reported structure‐property relationship in oxadiazole‐, thiadiazole‐, and selenadiazole‐fused ICs. [ 19 ] Analogous di(furo/thieno/seleno‐pyrrolo)‐benzothiadiazole, [ 15,20–24 ] benzoselenadiazole, [ 20 ] and benzotriazole [ 25,26 ] have been synthesized using Cadogan cyclization [ 27 ] as a key step and incorporated into the conjugated copolymers, dyes, ladder conjugated polymers, [ 28 ] and non‐fullerene acceptors for organic photovoltaics. [ 29 ]…”

Section: Introductionmentioning

confidence: 99%

Triazole‐fused indolo[2,3‐a]carbazoles: synthesis, structures, and properties

Ghosh

Das

Kumar

et al. 2020

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

The synthesis, structure, and photophysical and electrochemical properties of triazole fused indolo[2,3‐a]carbazole derivatives 2‐5 are reported. The key step involved in the synthesis of triazole fused indolo[2,3‐a]carbazole derivatives is the Cadogan ring closing reaction. 2‐Hexyl‐5,6‐dinitro‐2H‐benzo[d][1,2,3]triazoles having 4,7‐diaryl capping were subjected to the Cadogan cyclization reaction to obtain compounds 2‐5. In contrast to thiadiazole‐fused indolo[2,3‐a]carbazole 1, bromination of triazole‐fused indolo[2,3‐a]carbazole 4 afforded only meta‐dibrominated product with respect to the nitrogen of fused pyrrole rings on treatment with both N‐bromosuccinimide (NBS) and elemental bromine. These compounds showed positive solvatochromism in their emission spectra. Incorporation of electron‐donating substituent in the indole moiety resulted in the elevation of the highest occupied molecular orbital (HOMO) level. Density functional theory (DFT) calculations were performed to support the experimental findings.

show abstract

“…This behavior can be ascribed to their heteroaromatic characteristics and the presence of polarizable imine groups (C]N). Thereby, DA polymers emerge as an attractive type of material due to the availability of viable synthesis routes (e.g., by chemical or electrochemical methods), appropriate environmental stability, good conductivity characteristics and chemical functionality (Ghosh, Das, Kumar, Agrawal, & Zade, 2017;. Interestingly, this type of polymers has been reported as metal-free systems to catalyze light-induced reactions (e.g., hydrogen evolution).…”

Section: Introductionmentioning

confidence: 99%

Optical, morphological and photocatalytic properties of biobased tractable films of chitosan/donor-acceptor polymer blends

Jessop

Albornoz

Ramírez

et al. 2020

Carbohydrate Polymers

View full text Add to dashboard Cite

Biobased tractable films consisting of blends of chitosan (CS) with polymer bearing carbazole derivatives as pendant groups and fluorene-thiophene as donor-acceptor units (referred to as DA) were prepared, and their optical, morphological and photocatalytic properties were studied. DA was dissolved in tetrahydrofuran (THF) and mixed with an acidified aqueous solution containing chitosan to obtain chitosan/DA (CS/DA) films by solution casting. The fabricated biobased films were characterized using spectroscopic techniques (FT-IR and UV-vis), thermogravimetry, mechanical assays, contact angle analysis, and atomic force microscopy (AFM). The effects of varying DA compositions and the results of exposure to visible-light irradiation of the films were also analyzed. The results indicated the existence of interactions between chitosan and DA and a potentially profitable light-driven response of these biobased films. This behavior was reflected in the optical, topographical, and contact angle properties of the films, which exhibited different characteristics before and after visible-light exposure. Finally, the photocatalytic performance of the biobased films was tested via the decomposition of methyl orange (MO), as a reaction model system. Our results revealed a significant photocatalytic activity (according to biobased film composition, approximately 64 % and 87 % of methyl orange were degraded under continuous visible-light irradiation for 120 min) of the films which is attributed to the combined presence and synergetic effects of the film-forming ability of chitosan and the photoproperties of DA.

show abstract

Effect of heteroatom (S/Se) juggling in donor–acceptor–donor (D–A–D) fused systems: synthesis and electrochemical polymerization

Abstract: Planarization of donor–acceptor–donor (D–A–D) systems through N-bridges with systematic alteration of S/Se atom(s) resulted in interesting fluorosolvatochromic molecules and their electrochemical polymers.

Cited by 27 publications

References 39 publications

Effect of the donor units on the properties of fluorinated acceptor based systems

Effect of the donor units on the properties of fluorinated acceptor based systems

Triazole‐fused indolo[2,3‐a]carbazoles: synthesis, structures, and properties

Optical, morphological and photocatalytic properties of biobased tractable films of chitosan/donor-acceptor polymer blends

Contact Info

Product

Resources

About