Oligofuran-containing molecules for organic electronics

Gidron, Ori; Dadvand, Afshin; Sun, Emily Wei-Hsin; Chung, Insik; Shimon, Linda J. W.; Bendikov, Michael; Perepichka, Dmitrii F.

doi:10.1039/c3tc00079f

Cited by 81 publications

(68 citation statements)

References 65 publications

(57 reference statements)

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“…Indeed, the calculated maximum hole mobility in the b axial direction is nearly 17 times larger in 6 F (0.167 cm 2 V À1 s À1 ) than in 6 T (0.009 cm 2 V À1 s À1 ), while in the c axial direction the calculated mobility of 6 F (0.010 cm 2 V À1 s À1 ) is only slightly larger than that of 6 T (0.006 cm 2 V À1 s À1 ). [48,49] Generally, the FET mobility values for oligofurans were found to be similar in both classes of materials, when measured under similar conditions (with typical range of % 10 À2 cm 2 V À1 s À1 and on/off ratio of % 10 5 for polycrystalline films). Table 2 lists representative example devices (OFET and organic solar cells) with furan-containing oligomers and polymers.…”

Section: Theoretical Aspectsmentioning

confidence: 68%

“…Table 2 lists representative example devices (OFET and organic solar cells) with furan-containing oligomers and polymers. These works [48,49] provided evidence that, contrary to accepted opinion, [43b, 50] the presence of a large polarizable element, such as sulfur, is not a prerequisite for successful OFET materials based on conjugated heterocyclic molecules. [48,49] Generally, the FET mobility values for oligofurans were found to be similar in both classes of materials, when measured under similar conditions (with typical range of % 10 À2 cm 2 V À1 s À1 and on/off ratio of % 10 5 for polycrystalline films).…”

Section: Theoretical Aspectsmentioning

confidence: 85%

“…[48,49] This observation combined with a high on/off ratio and a low threshold voltage in oligofuran-based OFETs sets a starting point for future development of OLETs. [48,49] This observation combined with a high on/off ratio and a low threshold voltage in oligofuran-based OFETs sets a starting point for future development of OLETs.…”

Section: Devices Based On Long Oligofurans and Oligofuran-containing mentioning

confidence: 96%

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α‐Oligofurans: An Emerging Class of Conjugated Oligomers for Organic Electronics

2014

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While the field of organic electronics has developed extensively in recent years, it remains limited by number of materials available. Further expansion requires the innovation of new types of π-conjugated backbones, but suitable candidates are discovered only very rarely. The recent introduction of a new class of conjugated materials, long α-oligofurans, was therefore greeted with considerable interest. α-Oligofurans possess many of the properties required to excel in applications as organic electronic materials, can be manufactured from renewable resources, and are expected to be biodegradable. This Minireview provides an account of long oligofurans from the perspectives of their synthesis, molecular properties, chemical reactivity, and use in electronic devices.

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Section: Theoretical Aspectsmentioning

confidence: 68%

Section: Theoretical Aspectsmentioning

confidence: 85%

Section: Devices Based On Long Oligofurans and Oligofuran-containing mentioning

confidence: 96%

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α‐Oligofurans: An Emerging Class of Conjugated Oligomers for Organic Electronics

2014

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“…Nowadays the development of active and controllable materials for Non‐Linear Optics (NLO) is the subject of intensive investigations from both the theoretical and practical points of view, for their potential applications in the domain of optoelectronics and photonics . Although different classes of materials have been studied, the attention has recently shifted to organic materials as the molecular design can tailor the NLO responses for targeted applications …”

Section: Introductionmentioning

confidence: 99%

New Styryl Phenanthroline Derivatives as Model D−π−A−π−D Materials for Non‐Linear Optics

et al. 2018

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Four novel push-pull systems combining a central phenanthroline acceptor moiety and two substituted benzene rings, as a part of the conjugated π-system between the donor and the acceptor moieties, have been synthetized through a straightforward and efficient one-step procedure. The chromophores display high fluorescence and a peculiar fluorosolvatochromic behaviour. Ultrafast investigation by means of state-of-the-art femtosecond-resolved transient absorption and fluorescence up-conversion spectroscopies allowed the role of intramolecular charge transfer (ICT) states to be evidenced, also revealing the crucial role played by both, the polarity and proticity of the medium on the excited state dynamics of the chromophores. The ICT processes, responsible for the solvatochromism, also lead to interesting non-linear optical (NLO) properties: namely great two photon absorption cross-sections (hundreds of GM), investigated by the Two Photon Excited Fluorescence (TPEF) technique, and large second order hyperpolarizability coefficients, estimated through a convenient solvatochromic method.

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“…12,13,31 We have chosen the latter because bis(triarylamine) monocations tend to give intervalence absorption bands that are readily detectable. In Scheme 1 the amine end-capped selenophenes that were investigated in the present study (1,2,3,4) are shown along with thiophene analogs (I, II, IV), which we have previously explored. 23 Selenophenes 1−3 were investigated by a combination of cyclic voltammetry, optical absorption, EPR spectroscopy, and Kohn-Sham density functional theory (KS-DFT) calculations.…”

Section: ■ Introductionmentioning

confidence: 99%

Charge Delocalization in an Organic Mixed Valent Bithiophene Is Greater Than in a Structurally Analogous Biselenophene

et al. 2014

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A series of selenophenes with redox-active amine end-capping groups was synthesized and investigated. A combination of cyclic voltammetry, optical absorption, EPR spectroscopy, and quantum-chemical calculations based on Kohn-Sham density functional theory was used to explore charge delocalization in the monocationic mixed-valence forms of these selenophenes, and the results were compared to those obtained from analogous studies of structurally identical thiophenes. The striking finding is that the comproportionation constant (Kc) for the experimentally investigated biselenophene is more than 2 orders of magnitude lower than for its bithiophene counterpart (in CH3CN with 0.1 M TBAPF6), and the electronic coupling between the two amine end-capping groups in the mixed-valent biselenophene monocation is only roughly half as strong as in the corresponding bithiophene monocation. These are surprisingly large differences given the structural similarity between the respective biselenophene and bithiophene molecules. However, the computationally determined comproportionation constants for biselenophene and bithiophene are almost identical, and the electronic coupling in the monocationic biselenophene is only slightly smaller than that in the monocationic bithiophene. We assume that the external electric field may be responsible for the differences in monocation stabilities between experiment and computation. Our findings indicate that charge delocalization across individual selenophenes tends to be less pronounced than across individual thiophenes, and this may have important implications for long-range charge transfer across selenophene oligomers or polymers.

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Oligofuran-containing molecules for organic electronics

Cited by 81 publications

References 65 publications

α‐Oligofurans: An Emerging Class of Conjugated Oligomers for Organic Electronics

α‐Oligofurans: An Emerging Class of Conjugated Oligomers for Organic Electronics

New Styryl Phenanthroline Derivatives as Model D−π−A−π−D Materials for Non‐Linear Optics

Charge Delocalization in an Organic Mixed Valent Bithiophene Is Greater Than in a Structurally Analogous Biselenophene

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