Low bandgap poly(thienylenemethine) derivatives bearing terarylene moieties in the side chains

Ahn, Sangbum; Yabumoto, Kazuki; Jeong, Yongsoo; Akagi, Kazuo

doi:10.1039/c4py00849a

Cited by 16 publications

(10 citation statements)

References 44 publications

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“…Conversely, the highest occupied molecular orbital (HOMO) energy level for PQuT‐BT (−5.11 eV) is slightly higher than that of PQuT‐T (−5.24 eV), which is likely due to the increase in the number of electron‐donating thiophene spacers in the repeating unit. CV measurement of the polymers revealed redox amphoterism, meaning that the materials can be both oxidized and reduced with a narrow range of oxidation and reduction potentials . The amphoterism and low band gaps of quinoidal polymers have implications for their ambipolar charge transport, which will be discussed below.…”

Section: Methodsmentioning

confidence: 92%

π‐Conjugated Polymers Incorporating a Novel Planar Quinoid Building Block with Extended Delocalization and High Charge Carrier Mobility

Kim

Hwang

Kim³

et al. 2018

Advanced Materials

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Two novel conjugated polymers incorporating quinoidal thiophene are successfully synthesized. By combining 1D nuclear magnetic resonance (NMR) and 2D nuclear Overhauser effect spectroscopy analyses, the isomeric form of the major quinoid monomer is clearly identified as the asymmetric Z, E-configuration. The quinoidal polymers are synthesized via Stille polymerization with thiophene or bithiophene. Both quinoidal polymers exhibit the low band gap of 1.45 eV and amphoteric redox behavior, indicating extended conjugation owing to the quinoidal backbone. These quinoidal polymers show ambipolar behaviors with high charge carrier mobilities when applied in organic field-effect transistors. In addition, the radial alignment of polymer chains achieved by off-center spin-coating leads to further improvement of device performance, with poly(quinoidal thiophene-bithiophene) exhibiting a high hole mobility of 8.09 cm V s , which is the highest value among the quinoidal polymers up to now. Microstructural alteration via thermal annealing or off-center spin-coating is found to beneficially affect charge transport. The enhancement of crystallinity with strong π-π interactions and the nanofibrillar structure arising from planar well-delocalized quinoid units is considered to be responsible for the high charge carrier mobility.

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Section: Methodsmentioning

confidence: 92%

π‐Conjugated Polymers Incorporating a Novel Planar Quinoid Building Block with Extended Delocalization and High Charge Carrier Mobility

Kim

Hwang

Kim³

et al. 2018

Advanced Materials

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“…It is worth noting that all monomers developed so far have EDOT or its analogs, [9][10][11][29][30][31][32][33][34][35][36][37] which would restrict its further modification or application because of the difficulty of functionization on EDOT or on its analogs building blocks. Generally, conjugated poly(bis-thiophene methine)s [38][39][40][41][42] derivatives are frequently synthesized through acid-catalyzed polycondensation of thiophen derivatives with aromatic aldehydes and electrochemical polymerization of bis[2-(3,4-ethylenedioxy)thienyl]methine in solution phase. 40 Here, only simple thiophene or its derivatives containing monomers are synthesized and investigated.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of poly(bis‐thiophene methine)s via facile C–C bulk polymerization and their application as chemosensors for acid detection

Peng

Pei

Huang

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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Up to now, 3,4‐ethylenedioxythiophene (EDOT) or its modified analogs are indispensable units or subunits in all successful monomers for polythiophene synthesis through solid‐state polymerization (SSP). Here, a more open thiophene‐(CH(R))‐thiophene platform was developed successfully and corresponding poly(bis‐thiophene methine)s were obtained via C–C SSP or melt‐state polymerization (MSP), that is, bulk polymerization. Meanwhile, the observation of quite long effective Br–Br distance of 5.634 Å, which is more than 50% of halogen's double van der Waals radius (2rw), would help us to understand powerful capability of modulation of molecule movement and reaction under SSP. In addition, these polymers were further employed as acid sensors and they show highly sensitive response to HCl, MeSO3H, BF3‐OEt2, and HNO3. The detailed experiment reveals that P1 has the detection limit of 3.35 × 10−5 M for HCl. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1676–1683

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“…The molecular weights of the polymers were measured by GPC using chloroform as the mobile phase (Table ). BODIPY containing polymers via the Sonogashira polymerization often obtained with low molecular weights . It is true in these cases, however, 1 H NMR spectra show broadening of the peaks, indicating the formation of the polymers.…”

Section: Resultsmentioning

confidence: 99%

Site-selective synthesis and characterization of BODIPY-acetylene copolymers and their transistor properties

Debnath

Singh

Bedi

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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To study the effect of site-selective copolymerization of borondipyrromethene (BODIPY) with acetylene on the structural and optoelectronic properties, three copolymers P1-P3 were synthesized by the Sonogashira cross-coupling of BODIPY units with diacetylene and bromine capping through all the possible linkages: a-a (P1), a-b (P2), and b-b (P3). The optoelectronic properties of the polymers were investigated systematically to understand the effect of site-selective polymerization. The HOMO levels of the polymers were significantly tuned from P1 to P3 with negligible change in the LUMO levels. Broadening of absorption spectra from P3 to P1 was observed because of increase in the extent of conjugation.Additionally, the charge transport properties of these polymers in organic thin-film transistors (OTFTs) revealed that P1 and P3 exhibited only p-type mobility, whereas P2 exhibited electron mobility. Notably, the further investigations of the surface morphology of polymer films by atomic force microscopy (AFM) unveiled that comb like nanostructural arrangements in P3 was beneficial for the charge-carrier mobility over the circular arrangements in P1 and P2.

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Low bandgap poly(thienylenemethine) derivatives bearing terarylene moieties in the side chains

Abstract: Novel low bandgap poly(thienylenemethine) derivatives bearing terphenylene moieties in the side chains were synthesised. The bandgaps were controlled by introducing quinoidal structures into the benzonoidal main chains.

Cited by 16 publications

References 44 publications

π‐Conjugated Polymers Incorporating a Novel Planar Quinoid Building Block with Extended Delocalization and High Charge Carrier Mobility

π‐Conjugated Polymers Incorporating a Novel Planar Quinoid Building Block with Extended Delocalization and High Charge Carrier Mobility

Functionalization of poly(bis‐thiophene methine)s via facile C–C bulk polymerization and their application as chemosensors for acid detection

Site-selective synthesis and characterization of BODIPY-acetylene copolymers and their transistor properties

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