Fused Oligothiophenes

Skabara, Peter J.

doi:10.1002/9780470745533.ch3

Cited by 13 publications

(10 citation statements)

References 146 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The fused core of 1 and 2 has reduced the effective conjugation length of the molecules and as such, lowered the HOMO levels slightly (0.24 eV). The thieno[3,2- b ]thiophene unit has a higher aromatic stabilization energy than a single thiophene unit and this serves to lower the HOMO level and thus widen the HOMO−LUMO gap. There is some discrepancy between the HOMO−LUMO gap calculated optically and that determined electrochemically ( ca.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-b]thiophene End-Capped with EDOT and EDTT Units

et al. 2010

Self Cite

View full text Add to dashboard Cite

This version is available at https://strathprints.strath.ac.uk/28454/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. within the materials and also the packing of the molecules in the solid state. CGL-TOF studies give hole mobilities up to 4 × 10 -5 cm 2 V -1 s -1 for compound 1 and 1.5 × 10 -5 cm 2 V -1 s -1 for 2.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-b]thiophene End-Capped with EDOT and EDTT Units

et al. 2010

Self Cite

View full text Add to dashboard Cite

show abstract

“…For comparison, the optical band gap of P32, in which the heteroatom in the peripheral ring is sulfur, is 0.85 eV. 33 Polyselenophene based polymers P41−42 exhibit very low band gaps of 0.72 and 0.76 eV, respectively compared to P32 and P40. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring in polymer chain, which stabilized the quinoid structure.…”

Section: Fused Polyselenophenes Zade Et Al Reported An Efficient Synt...mentioning

confidence: 99%

Poly(3,4-ethylenedioxyselenophene) and Its Derivatives: Novel Organic Electronic Materials

2014

View full text Add to dashboard Cite

Since the discovery of high conductivity in iodine-doped polyacetylene, many interesting conducting polymers have been developed. Of these, polythiophenes have been most studied as electronic materials, with poly(3,4-ethylenedioxythiophene) (PEDOT) and the water-soluble PEDOT-PSS being the most successful commercially used conducting polymers. The polyselenophene family together with poly(3,4-ethylenedioxyselenophene) (PEDOS) and its derivatives have been shown to have slightly different properties compared to these of polythiophene and PEDOT because of their different electron donating characters, aromaticities (selenophene vs thiophene), oxidation potentials, electronegativities, and polarizabilities (Se vs S). As a result, the polyselenophenes, especially PEDOS and its derivatives, show a lower band gap and higher-lying highest occupied molecular orbital (HOMO) levels compared with those of thiophene and the PEDOT family. In an organic materials context, the PEDOS family offers some advantages over PEDOT derivatives. This Account draws on computational studies, synthetic methods, electrochemical polymerizations, chemical polymerizations, and the materials properties of PEDOS and its derivatives to demonstrate the importance of these novel materials, which lie at the frontier of conducting polymer research. In particular, we show that (i) PEDOS derivatives have a lower band gap (about 0.2 eV) than the corresponding PEDOT derivatives. Consequently, PEDOS derivatives can absorb the solar spectrum more efficiently compared to PEDOT derivatives and the properties of optoelectronic devices based on neutral and doped PEDOS should be somewhat different from these of PEDOT. (ii) EDOS derivatives have a greater tendency to undergo electrochemical polymerization compared to EDOT derivatives and offer stable and smooth polymer films. (iii) The PEDOS backbone is more rigid than the PEDOT backbone. (iv) PEDOS derivatives are excellent electrochromic materials with high transparency, and have higher contrast ratio and coloration efficiency. (v) The PEDOS/C electrode offers better control over the formation and size of nanoparticles through Se···Pt interactions compared with the PEDOT/C electrode. In addition to this, we summarize the synthesis, electrochemical polymerization, materials properties, and computational studies of fused polyselenophene analogues, namely, poly(cyclopenta[c]selenophene), and a series of low band gap thieno- or selenolo-fused polyselenophenes and selenolo-fused polythiophene. Additionally, we discuss oxidative and solid state polymerization to obtain conducting PEDOS, and its derivatives, and made throughout comparison with S-analogue where applicable. We found that EDOS-based derivatives have a greater tendency toward solid state polymerization and working at a temperature about 20 °C lower than that required for EDOT-based compounds. Our results demonstrate the utility of EDOS unit for generating promising materials PEDOS and its derivatives for electronic devices. Consequently, EDOS structure is ...

show abstract

“…However, PITN is not planar , because of repulsion between the sulfur atom and hydrogen atom on the phenyl ring and, consequently, its band gap is above 1.0 eV. Another example is thieno-fused thiophenes, such as poly(2-phenylthieno[3,4- b ]thiophene) ( P1 ) and poly(2-decylthieno[3,4- b ]thiophene) ( P2 ), which are expected to be planar. Using this strategy, Sotzing and co-workers reported two unsubstituted thieno- and furan-fused polythiophene-based polymers, poly(thieno[3,4- b ]thiophene) (PT34bT; P3 ) , and poly(thieno[3,4- b ]furan) (PT34bF) having low band gaps of 0.85 and 1.03 eV, respectively.…”

Section: Introductionmentioning

confidence: 99%

Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

Patra¹,

Wijsboom²,

Leitus³

et al. 2011

Chem. Mater.

178

107

View full text Add to dashboard Cite

A series of new low-band-gap thieno-or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br 2 , 5Br 2 , and 6Br 2 ) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (∼0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

show abstract

Fused Oligothiophenes

Cited by 13 publications

References 146 publications

Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-b]thiophene End-Capped with EDOT and EDTT Units

Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-b]thiophene End-Capped with EDOT and EDTT Units

Poly(3,4-ethylenedioxyselenophene) and Its Derivatives: Novel Organic Electronic Materials

Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

Contact Info

Product

Resources

About