Effects of Molecular Structure on Intramolecular Charge Carrier Transport in Dithieno [3,2-<i>b</i>: -<i>d</i>] Pyrrole-Based Conjugated Copolymers

Honsho, Yoshihito; Saeki, Akinori; Seki, Shu

doi:10.1155/2012/983523

Cited by 6 publications

(3 citation statements)

References 38 publications

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“…27 The structure consists of a thiophene-pyrrole-thiophene fused ring system, it exhibits extended conjugation, high electron donor character along with availability for functionalization. 28 The progress made in synthesis of this type structures along with their optoelectronic properties was previously addressed. 29 The reports include preparation of DTP-alkyl-NH 2 , DTP-aryl-NH 2 and DTP-alkyl-DTP.…”

Section: The Novelty/significance Of Thiophene-pyrrole Hybrid Structuresmentioning

confidence: 99%

“…This type of structures has been proven as the most favorable due to effective conjugation that allows the degree of coplanarity necessary for maintaining electrical conductivity 31 through intermolecular hopping of charge carriers 28 whilst maintaining the desired functionality. The electrochemical polymerization of the thiophene-pyrrole hybrids requires an oxidation potential lower than the thiophene parent molecule and can contribute to the stabilization of the oxidized state of the resulting polymer.…”

Section: The Novelty/significance Of Thiophene-pyrrole Hybrid Structuresmentioning

confidence: 99%

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Review—Functional Platforms for (Bio)sensing: Thiophene-Pyrrole Hybrid Polymers

Apetrei

Çamurlu

2020

J. Electrochem. Soc.

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The synthesis of thiophene-pyrrole hybrid polymers has become of increased interest due to their potential in a wide range of applications, from optoelectronics to biodevices. While the extended application of these materials in optoelectronics or photovoltaics has been previously addressed, a comprehensive account on their potential for application in sensorics has not been reported so far. The main advantages derived from their application are related to facility in synthesis and stable electrochemical behavior with the added benefit of tailor-made functionality. As it has become clear that the ultimate goal in electrochemical sensing is the preparation of a conducting platform that not only exhibits satisfactory conductivity but also contains functional groups that are able to connect to the desired bio-element, the hybrid polymers appear very promising. Preparation of conducting platforms with tailored functionality such as poly(2,5-di(thienyl)pyrrole)s and poly(dithieno(3,2-b:2′,3′-d)pyrroles)s represents an excellent opportunity for achieving stable immobilization and maintaining adequate orientation of biomolecules, whilst improving the electron transfer, resulting in highly sensitive and stable biosensors. The current review briefly addresses the synthesis of hybrid thiophene-pyrrole molecules detailing several approaches and, subsequently, focuses on their application as polymeric bioimmobilization platforms for electrochemical detection of relevant bio-analytes, bio-receptors or DNA hybridization events.

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Section: The Novelty/significance Of Thiophene-pyrrole Hybrid Structuresmentioning

confidence: 99%

Section: The Novelty/significance Of Thiophene-pyrrole Hybrid Structuresmentioning

confidence: 99%

Review—Functional Platforms for (Bio)sensing: Thiophene-Pyrrole Hybrid Polymers

Apetrei

Çamurlu

2020

J. Electrochem. Soc.

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“…[13][14][15] The influence of the molecular structure on intramolecular charge transfer in dithienopyrrole copolymers containing phenyl, 2,2′-biphenyl, thiophene, 2,2′dithiophene, and 9,9′-dioctylfluorene units was studied. 16 Bäuerle et al synthesized oligomers containing blocks of dithieno[3,2-b:2′,3′-d]pyrrole and thieno[3,2-b]pyrrole-4,6dione. 17 The use of furan as a spacer between thieno[3,2-b] pyrrole and alkylated diketopyrrolopyrroles was discussed by Biewer.…”

Section: Introductionmentioning

confidence: 99%

New polymers based on thieno[3,2-b]pyrrole derivatives and their electrochemical properties

Miftakhov,

Torosyan,

Gimalova

et al. 2023

Polym. Chem.

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Efficient Charge Transport Driven by Strong Intermolecular Interactions in Cyclopentadithiophene‐Based Donor–Acceptor Type Conjugated Copolymers

Lee

Luke

Ahn

et al. 2022

Adv Elect Materials

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as switching devices for innovative electronic applications such as flexible and stretchable electronics. [1][2][3][4] Mobilities in the early stages of OFET development were poor, with polyacetylene having a fieldeffect mobility of only ≈10 −5 cm 2 V −1 s −1 . However, since the development of thiophene-based semicrystalline polymer semiconductors (e.g., regioregular poly(3hexylthiophene-2,5-diyl) (rr-P3HT), poly(3,3'-dialkyl-quaterthiophene) (PQT), and poly(2,5-bis(3-alkylthiophen-2-yl) thieno[3,2-b]thiophene) (PBTTT)) and then donor-acceptor (D-A) type conjugated copolymers with alternating electron-donating and electron-accepting moieties along the polymer backbone, several research groups have reported high-performance semiconducting polymers with field-effect mobilities in excess of 10 cm 2 V −1 s −1 which is comparable to that of their soluble oxide-based inorganic semiconductors counterparts. [5,6] Indeed, the D-A type conjugated copolymers are intriguing materials because they possess superior mobility values to the thiophene-based semi-crystalline homopolymers, despite exhibiting somewhat amorphous-like structural characteristics. This means that their structure-property relationships may not follow the trend of higher mobilities requiring higher degrees of semicrystalline molecular order Understanding charge transport in π-conjugated polymers is critical for the design of high-mobility polymers. However, charge transport in donor-acceptor (D-A) type copolymers and the roles of D and A units are still unclear. Herein, the charge transport properties of three cyclopentadithiophene (CDT)-based D-A type copolymers with CDT as a common donor and benzothiadiazole, fluoro-2,1,3-benzothiadiazole, or pyridyl-2,1,3-thiadiazole (PTz) as an acceptor are investigated. The best charge transport is found for CDT-PTz showing 0.79 ± 0.01 cm 2 V −1 s −1 hole mobility in field-effect transistors, with the lowest energetic disorder by temperature-dependent mobility measurements. Using various structural probes and density functional theory simulations, it is found that CDT-PTz has the most rigid and planar backbone structure and the strongest intramolecular dipole moment thanks to the noncovalent N-S interactions and the strong electron-withdrawing PTz acceptor unit. These structural properties lead to strong intermolecular interactions in CDT-PTz, reducing its π-π stacking distance, producing strong aggregation even in hot dilute solutions. The enhanced mobility in CDT-PTz is attributed to this high quality π-π stacking, driven by increased backbone rigidity and strong molecular dipoles. This work suggests that rigidifying the copolymer backbone with enhanced push-pull strength of the D-A units is a key requirement for high-mobility D-A copolymers.

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Effects of Molecular Structure on Intramolecular Charge Carrier Transport in Dithieno [3,2-b: -d] Pyrrole-Based Conjugated Copolymers

Cited by 6 publications

References 38 publications

Review—Functional Platforms for (Bio)sensing: Thiophene-Pyrrole Hybrid Polymers

Review—Functional Platforms for (Bio)sensing: Thiophene-Pyrrole Hybrid Polymers

New polymers based on thieno[3,2-b]pyrrole derivatives and their electrochemical properties

Efficient Charge Transport Driven by Strong Intermolecular Interactions in Cyclopentadithiophene‐Based Donor–Acceptor Type Conjugated Copolymers

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