Neutral‐State Green Conjugated Polymers from Pyrrole Bis‐Substituted Benzothiadiazole and Benzoselenadiazole for Electrochromic Devices

Baran, Derya; Öktem, Gözde; Celebi, Selin; Toppare, Levent

doi:10.1002/macp.201000744

Cited by 35 publications

(25 citation statements)

References 33 publications

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“…BT oligomers have slightly reduced chain length dependence and the smallest band gap reductions are found with CDM and IFDMT. Trends in HOMO−LUMO gaps parallel those of the first excitation energy, but the individual chain lengths dependencies of HOMOs and LUMOs vary 78 1.64 3.16…”

Section: ■ Resultsmentioning

confidence: 95%

Effect of Donor–Acceptor Substitution on Optoelectronic Properties of Conducting Organic Polymers

Salzner

2014

J. Chem. Theory Comput.

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The impact of donor-acceptor substitution on optical and electronic properties of conducting polymers was investigated with time-dependent density functional theory (TDDFT). A series of donor-acceptor systems with thiophene, 3,4-ethylenedioxythiophene, and pyrrole as donors and 3,4-difluorothiophene, diketopyrrolopyrrole, 2,1,3-benzothiadiazole, 4-dicyanomethylene-4H-cyclopenta[2,1-b;3,4-b']dithiophene, and indeno[1-2b]-fluorene-6,12-dimalonitrile as acceptors as examples of donor-acceptor systems with increasing donor-acceptor character was studied. Spectral properties were analyzed in terms of differences in ionization potentials and electron affinities of donors and acceptors, charge separations between donors and acceptors in ground and excited states, and electron distribution in the acceptor units. A shift in electron density away from the backbone caused by some of the acceptors correlates with localization of the conduction band on the acceptor. Localization does not correlate with energy level differences between donor and acceptor. Localization results in shift of oscillator strength from the HOMO-LUMO peak to a higher energy feature where the first delocalized orbital acts as the acceptor. The "camel back" absorption with two equally strong peaks that gives rise to green polymers is the intermediate case associated with partial localization of the conduction band. Stronger localization causes the HOMO-LUMO band to almost vanish.

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Section: ■ Resultsmentioning

confidence: 95%

Effect of Donor–Acceptor Substitution on Optoelectronic Properties of Conducting Organic Polymers

Salzner

2014

J. Chem. Theory Comput.

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“…Many factors might result to the phenomenon, such as the powers of the acceptor units, heavy atom substitution, the aromaticity, etc. [8,38,45].…”

Section: Electrochemical Activity Of Polymer Filmsmentioning

confidence: 97%

Furan and pyridinechalcogenodiazole-based π-conjugated systems via a donor-acceptor approach

Liu

Zhen

Ming

et al. 2016

J Solid State Electrochem

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Two novel furan and pyridinechalcogenodiazole based monomers, namely 4,7-di(furan-2-yl)-[1, 2, 5]thiadiazolo [3,4-c]pyridine (Fu-S-Fu) and 4,7-di(furan-2-yl)-[1, 2, 5]selenadiazolo [3,4-c]pyridine (Fu-Se-Fu), where a single atom in the pyridinechalcogenodiazole unit is varied from S to Se, were designed and synthesized via a donoracceptor approach, and then the corresponding polymers, P(Fu-S-Fu) and P(Fu-Se-Fu), were electrosynthesized. Also, structure characterization and optoelectronic properties, including FTIR, SEM, DFT theoretical calculations, intramolecular charge transfer nature, optical and electrochemical behaviors, and electrochromic performance, were systematically investigated and comparatively discussed. The obtained monomers exhibited lower oxidation potential (Fu-S-Fu: 1.12 V; Fu-Se-Fu: 1.09 V), leading to the facile electrodeposition of uniform hybrid polymer films with outstanding electroactivity at low oxidation potentials. Optical spectroscopy of corresponding polymers showed that Se substitution led to a redshift in the low-energy transition, while the high-energy band remains relatively constant in energy.

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“…According to these results, changing the electron-deficient unit of the polymer significantly altered the reduction potential of the polymers. Thus, LUMO levels responded differently and consequently PCBSe has a lower band gap value compared with PCBS and PCBN because of the stronger electron-withdrawing character of benzoselenadiazole moiety [26][27][28]. On the other hand, semi reversible oxidation peaks were found at E Table 2, it can be deduced that electrochemical and optical behaviors of the polymers were significantly affected by varying the heteroatom on the acceptor moiety attached to the carbazole-donor main chain.…”

Section: Electrochemical Properties Of Pcbx Polymersmentioning

confidence: 99%

Carbazole based electrochromic polymers with benzoazole units: Effect of heteroatom variation on electrochromic performance

Doyranlı¹,

Koyuncu²

2016

Express Polym. Lett.

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Abstract.A series of carbazole-based polymers were synthesized via Suzuki polymerization between N-(2-ethylhexyl)carbazole-3,6-bis(ethyleneboronate) (Cbz) and dibromobenzazole unit. Three different polymers, PCBN, PCBS and PCBSe were obtained from 4,7-dibromo-2-hexyl-2H-benzotriazole (BN), 4,7-dibromo-2,1,3-benzothiadiazole-(BS) and 4,7-dibromo-2,1,3-benzoselenadiazole (BSe), respectively. It is observed that, the variation of heteroatoms (N,S and Se) on the benzazole unit have most important effect on electro-optic properties of the PCBX polymers. Neutral state color of the polymer films and their electrochromic performances are also influenced. Among the synthesized polymers, the PCBS bearing 2,1,3-benzothiadiazole as acceptor units has a broad absorption and 50% of ΔT in the near-IR regime at the oxidized state. This property of PCBS is a great advantage for near-IR electrochromic applications.

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Neutral‐State Green Conjugated Polymers from Pyrrole Bis‐Substituted Benzothiadiazole and Benzoselenadiazole for Electrochromic Devices

Cited by 35 publications

References 33 publications

Effect of Donor–Acceptor Substitution on Optoelectronic Properties of Conducting Organic Polymers

Effect of Donor–Acceptor Substitution on Optoelectronic Properties of Conducting Organic Polymers

Furan and pyridinechalcogenodiazole-based π-conjugated systems via a donor-acceptor approach

Carbazole based electrochromic polymers with benzoazole units: Effect of heteroatom variation on electrochromic performance

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