New Type of Donor-Acceptor Through-Space Conjugated Polymer

Lin, Lin; Morisaki, Yasuhiro; Chujo, Yoshiki

doi:10.1155/2010/908128

Cited by 5 publications

(3 citation statements)

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“…Much interest has recently been directed to through-space conjugation in face-to-face aromatics [35] including cyclophanes, [36] hexaarylbenzenes, [37] helical foldamers [38] and others, due to their capacities to transport charges and energies via a spatial channel. [39] Interplane distances of πstacked aromatic systems of 280 pm in cyclophanes [40] up to 349.4 pm [35] in π-stacked aromatics have been measured. In contrast to the aforementioned systems, the through-space conjugation in mesomeric betaine 29 o is enabled by the proximity of the 2-positions of the thiophenes and not by πstacking between the pyridinium and the phenolate which required the formation of another conformer.…”

Section: Resultsmentioning

confidence: 99%

Switchable Mesomeric Betaines Derived from Pyridinium‐Phenolates and Bis(thienyl)ethane

et al. 2021

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Syntheses of push-pull substituted non-symmetric bis(thienyl) ethenes (BTEs) possessing a central perfluorocyclopentene core are described. The substituent effects of anisole, phenole, and phenolate as well as pyridine, pyridinium, and N-methylpyridinium substituents, joined through their 3-or 4-positions to the central BTE core, respectively, cover the range from very strongly electron-donating [σ(4-phenolate) = À 1.00] to extremely strongly electron-withdrawing [σ(pyridinium-4-yl) = + 2.57] in the title mesomeric betaines. The different isomers possessing 4-yl/4-yl, 4-yl/3-yl and 3-yl/3-yl substituents represent different combinations of conjugated and cross-conju-gated partial structures and cause different spectroscopic properties. In addition, through-space conjugation between the 2-and 2'-position of the thiophenes can be observed which circumvents the charge-separation of through-bond crossconjugation. The BTE possessing the push-pull chromophore consisting of 3-anisole and 4-pyridinium substituents (24) displays the best extinction coefficients within the series of compounds described here (ɛ = 33.8/15.7 L/mol • cm), while the mesomeric betaine possessing an N-methylpyridinium-4-yl and a 4-phenolate substituent (29) displays considerable bathochromic shifts to λ max = 724 nm in its closed form.

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Section: Resultsmentioning

confidence: 99%

Switchable Mesomeric Betaines Derived from Pyridinium‐Phenolates and Bis(thienyl)ethane

et al. 2021

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“…Especially, selection of D–A moieties enables control of the highest occupied molecular orbital (HOMO) energy and lowest unoccupied molecular orbital (LUMO) energy and thus the band gap energy (difference between HOMO and LUMO). Determination of the HOMO–LUMO energy level has an importance in terms of the optimized charge injection into and charge extraction out of the conducting polymer layer. , Moreover, band gap energy shows the absorption edge which is an important parameter for the optoelectronic application of conducting polymers.…”

Section: Introductionmentioning

confidence: 99%

“…Determination of the HOMO–LUMO energy level has an importance in terms of the optimized charge injection into and charge extraction out of the conducting polymer layer. 5 , 13 Moreover, band gap energy shows the absorption edge which is an important parameter for the optoelectronic application of conducting polymers.…”

Section: Introductionmentioning

confidence: 99%

Design Principles for the Acceptor Units in Donor–Acceptor Conjugated Polymers

Hacıefendioǧlu

Yıldırım

2022

ACS Omega

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More than 50 different acceptor units from the experimental literature have been modeled, analyzed, and compared by using the computationally extracted data from the density functional theory (DFT) perspective for tetramer structures in the form of (D−B−A−B) 4 (D, donor; A, acceptor; B, bridge) with fixed donor and bridge units. Comparison of dihedral angle between acceptor, donor, and bridge units, bond order, and hyperpolarizability reveals that these three structural properties have a dominant effect on the frontier electronic energy levels of the acceptor units. Systematic investigation of the structural properties has demonstrated the band gap energy dependency of the acceptor units on the planarity, conjugation, and the electron delocalization. Substitution effect, morphological alternation, and insertion of π-electron deficient atoms in A unit have also an important role to determine physical properties of the donor−acceptor conjugated polymers. This benchmark study will be beneficial for the band gap engineering and molecular design of the donor−acceptor copolymers using different acceptor units for the organic electronic applications.

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Synthesis and photovoltaic device studies of azo‐linked low‐bandgap polymers

Meena

Alam

Dutta

et al. 2016

Polymer International

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We report the synthesis of a series of new polymers containing azo linkage as a part of the main chain. The monomer 1,2‐bis(7‐bromo‐9,9‐dioctyl‐9H‐fluoren‐2‐yl)diazene was synthesized using a precursor approach which avoids non‐selective bromination and was copolymerized with various donor or acceptor units. The homopolymer poly[1,2‐bis(9,9‐dioctyl‐9H‐fluoren‐2‐yl)diazene] (P1) as well as the copolymers poly[1‐(9,9‐dioctyl‐9H‐fluoren‐2‐yl)‐2‐(9,9,9′,9′‐tetraoctyl‐9H,9′H‐[2,2′‐bifluoren]‐7‐yl)diazene] (P2), poly[1‐(9,9‐dioctyl‐7‐(4‐octylthiophen‐2‐yl)‐9H‐fluoren‐2‐yl)‐2‐(9,9‐dioctyl‐9H‐fluoren‐2‐yl)diazene] (P3) and poly[4‐(7‐((9,9‐dioctyl‐9H‐fluoren‐2‐yl)diazenyl)‐9,9‐dioctyl‐9H‐fluoren‐2‐yl)benzo[c][1,2,5]thiadiazole] (P4) were synthesized by Suzuki polymerization. The copolymers poly[1‐(7‐(4,4‐dioctyl‐4H‐cyclopenta[1,2‐b:5,4‐b′]dithiophen‐2‐yl)‐9,9‐dioctyl‐9H‐fluoren‐2‐yl)‐2‐(9,9‐dioctyl‐9H‐fluoren‐2‐yl)diazene] (P5) and poly[4‐(5‐(7‐((9,9‐dioctyl‐9H‐fluoren‐2‐yl)diazenyl)‐9,9‐dioctyl‐9H‐fluoren‐2‐yl)‐4‐octylthiophen‐2‐yl)‐7‐(4‐octylthiophen‐2‐yl)benzo[c][1,2,5]thiadiazole] (P6) were synthesized by direct arylation polymerization reaction. Polymers synthesized using the direct arylation method show good molecular weight, with absorption maxima in the range 500 to 532 nm. P5 and P6 possess low optical bandgaps of 1.81 and 1.86 eV, respectively. A power conversion efficiency of 0.53% with open circuit voltage of 0.53 V, short circuit current density of 3.1 mA cm−2 and fill factor of 29% has been achieved with C71‐PCBM as acceptor in bulk heterojunction solar cells fabricated with P5 as donor. © 2016 Society of Chemical Industry

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New Type of Donor-Acceptor Through-Space Conjugated Polymer

Cited by 5 publications

References 54 publications

Switchable Mesomeric Betaines Derived from Pyridinium‐Phenolates and Bis(thienyl)ethane

Switchable Mesomeric Betaines Derived from Pyridinium‐Phenolates and Bis(thienyl)ethane

Design Principles for the Acceptor Units in Donor–Acceptor Conjugated Polymers

Synthesis and photovoltaic device studies of azo‐linked low‐bandgap polymers

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