Functional Oligothiophene‐Based Materials: Nanoarchitectures and Applications

Mishra, Amaresh; Ma, Chang‐Qi; Segura, José L.; Bäuerle, Peter

doi:10.1002/9780470745533.ch1

Cited by 21 publications

(20 citation statements)

References 501 publications

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“…21,22 The reactions of 3, 4, and 5 with sodium sulfide afforded C12T, C16T, and C18T, respectively (Scheme 1). 21,22 The reactions of 3, 4, and 5 with sodium sulfide afforded C12T, C16T, and C18T, respectively (Scheme 1).…”

Section: Macrocyclic Cyclo[n]thiophenesmentioning

confidence: 99%

“…22 These p-expanded macrocycles possess shape-persistent p-frames, and electric and optoelectronic properties of the macrocycles largely depend on the inserted p-systems to the parent oligothiophene macrocycles. 22 These p-expanded macrocycles possess shape-persistent p-frames, and electric and optoelectronic properties of the macrocycles largely depend on the inserted p-systems to the parent oligothiophene macrocycles.…”

Section: Planar and Nonplanar Macrocyclesmentioning

confidence: 99%

“…The pioneering study on the synthesis of cyclo[n]thiophenes C12T, C14T, and C16T by Ba ¨uerle et al employed coppermediated coupling for the construction of macrorings, and the oxidative coupling of 1 or 2 yielded 3 and 5 or 4 and 6, respectively. 21,22 The reactions of 3, 4, and 5 with sodium sulfide afforded C12T, C16T, and C18T, respectively (Scheme 1). Computational studies predicted that syn-C8T-C12T possesses nearly planar structures.…”

Section: Macrocyclic Cyclo[n]thiophenesmentioning

confidence: 99%

“…Fully conjugated p-expanded oligothiophene macrocycles are a family closely related to redox-active oligothiophene macrocycles such as C[n]Ts, exhibiting potential optoelectronic application to organic light-emitting diodes (OLED), organic field-effect transistors (OFET), organic solar cells, and many others. 22 These p-expanded macrocycles possess shape-persistent p-frames, and electric and optoelectronic properties of the macrocycles largely depend on the inserted p-systems to the parent oligothiophene macrocycles. Although [n]cycloparaphenylenes (CPPs), cyclic [n]paraphenyleneacetylenes (CPPAs), and [4]cyclo-2,8-crysenylenes (CC 2,8 ) possess a 3D hoop-shaped conjugation with p-orbitals parallel to the macroring, p-orbitals of C[n]Ts containing a,a 0linkages are aligned perpendicular to the planar macroring.…”

Section: Planar and Nonplanar Macrocyclesmentioning

confidence: 99%

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Multifunctional π-expanded oligothiophene macrocycles

2015

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This tutorial review summarizes recent progress in the design, synthesis, and multifunctional properties of fully conjugated macrocyclic π-systems. We focus on the π-expanded oligothiophene macrocycles after a short survey of macrocyclic conjugated loops and belts such as [n]cycloparaphenylenes, cyclic[n]para-phenylacetylenes, [4]cyclo-2,8-crysenylenes, and cyclo[n]thiophenes. Fully conjugated π-expanded oligothiophene macrocycles possess shape-persistent but sometimes pliable π-frames, and the electronic and optoelectronic properties of the macrocycles largely depend on the π-systems inserted into the oligothiophene macrocycles. Among them, the π-expanded oligothiophene macrocycle composed of 2,5-thienylenes, ethynylenes, and vinylenes is one of the most widely applicable macrocycles for constructing multifunctional π-systems. These π-expanded oligothiophene macrocycles from small to very large ring sizes can be prepared via a short step procedure, and their various solid state structures can be determined by X-ray analysis. Since these macrocycles have inner and outer domains, specific information concerning structural, electronic, and optical properties is expected. Furthermore, π-expanded oligothiophene macrocycles with alkyl substituents exhibit various morphologies depending on nanophase separation of molecules, and a morphological change is observed for the molecular switch.

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Section: Macrocyclic Cyclo[n]thiophenesmentioning

confidence: 99%

Section: Planar and Nonplanar Macrocyclesmentioning

confidence: 99%

Section: Macrocyclic Cyclo[n]thiophenesmentioning

confidence: 99%

Section: Planar and Nonplanar Macrocyclesmentioning

confidence: 99%

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Multifunctional π-expanded oligothiophene macrocycles

2015

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“…6 In addition, thiophenes are also used in polymers and materials that have a potential application in the area of organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). 7–13 Selenophenes, a selenium analogue of thiophene, are also known to exhibit biological activities, such as anticancer, 14 antitumor, 15 antidepressant, 16 antioxidant, 17 and antiproliferative activities. 18 Benzo[ b ]selenophenes and selenophenes have a narrow HOMO-LUMO gap when compared with their sulfur analogues and have applications in photonics.…”

mentioning

confidence: 99%

Green synthesis of halogenated thiophenes, selenophenes and benzo[b]selenophenes using sodium halides as a source of electrophilic halogens

Kesharwani

Giraudy

Morgan

et al. 2017

Tetrahedron Letters

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Herein, we report the first synthesis of chlorinated benzo[b]selenophenes via environmentally friendly electrophilic chlorocyclization reaction using “table salt” as a source of “electrophilic chlorine” and ethanol as a solvent. In addition, the synthesis of diverse halogenated heterocycles, including 3-chloro, 3-bromo and 3-iodo thiophenes, selenophenes, and benzo[b]selenophenes was successfully accomplished under the same environmentally benign reaction conditions. This methodology has several advantages over other previously reported reactions as it employs simple starting compounds, an environmentally friendly solvent, ethanol, and non-toxic inorganic reagents under mild reaction conditions, resulting in the high product yields.

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Reversible Photoisomerization of Monolayers of π‐Expanded Oligothiophene Macrocycles at Solid–Liquid Interfaces

2018

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Self-assembled monolayers of a p-expanded oligothiophene macrocycle undergo photoisomerization between their Z,Z and E,E diastereomers at the interface between octanoic acid solutions and highly oriented pyrolytic graphite (HOPG). The switching process proceeds in situ at the solidliquid interface and was followed by scanning tunneling microscopy( STM). Upon illumination with light at 365 nm (546 nm), amonolayer of Z,Z-8mer (E,E-8mer) photoisomerizes to the E,E-8mer (Z,Z-8mer) form with changes in 2D hexagonal packing.These findings provideinsight towards the design of photoresponsive surfaces with desirable optoelectronic and structural (host-guest) properties.Scheme 1. Chemical structures of Z,Z-8mer and E,E-8mer.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/10.

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Functional Oligothiophene‐Based Materials: Nanoarchitectures and Applications

Cited by 21 publications

References 501 publications

Multifunctional π-expanded oligothiophene macrocycles

Multifunctional π-expanded oligothiophene macrocycles

Green synthesis of halogenated thiophenes, selenophenes and benzo[b]selenophenes using sodium halides as a source of electrophilic halogens

Reversible Photoisomerization of Monolayers of π‐Expanded Oligothiophene Macrocycles at Solid–Liquid Interfaces

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