Functional Macromolecules with Electron-Donating Dithiafulvene Unit

Uemura, Takashi; Naka, Kensuke; Chujo, Yoshiki

doi:10.1007/b12305

Cited by 15 publications

(11 citation statements)

References 105 publications

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“…Electroactive dithiafulvenes (4) derived from cycloaddition of a thioketene and its alkynethiol tautomer [45][46][47][48] can form 1,3dithiolium cations by an easy one-electron oxidation both chemically and electrochemically (Scheme 1). The reactive species dimerize to form a vinylogous TTF (5), which has an extended TTF structure involving an ethanediylidene unit in the central conjugation.…”

Section: Introductionmentioning

confidence: 99%

Functional polymers based on electron-donating TTF and derivatives

2007

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This review highlights the recent progress of electron-donating polymers containing thio-cyclic units (tetrathiafulvalene, dithiafulvene, thioketene dimers). These polymers with TTF derivatives in the main chain and side chain have been studied with the aim of improving processability of their charge transfer complexes and increasing the dimensionality of their conducting paths in the solid state. This review also highlights a novel synthetic methodology of the electroactive polymers, i.e., cycloaddition polymerization of bisthioketene to produce poly(dithiafulvene) and oxidative polymerization of bisdithiafulvenyl monomers and thioketene dimers. In the application of poly(dithiafulvene)s to the polymer-metal hybrid systems, they act as not only the reducing agent but also the stabilizer for the formed metal nanoparticles.

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Section: Introductionmentioning

confidence: 99%

Functional polymers based on electron-donating TTF and derivatives

2007

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“…1,4-Dithiafulvenes (DTFs) because of their excellent electrondonating properties [1][2][3][4] have been increasingly employed over the past years as active components in organic optoelectronic materials and devices such as chemical sensors, [5][6][7][8][9][10][11] molecular switches, [12][13][14][15] non-linear optic-phores, 16 photovoltaic cells, [17][18][19][20][21][22][23] eld-effect transistors (FETs), [24][25][26] and so forth. Besides acting as p-electron donors, DTFs also provide synthetic access to another intriguing class of tetrathiafulvalene (TTF) analogues, namely tetrathiafulvalene vinylogues (TTFVs), through a straightforward oxidative dimerization reaction.…”

Section: Introductionmentioning

confidence: 99%

“…8,[27][28][29] As illustrated in Scheme 1, a phenyl-substituted DTF 1 can readily undergo single-electron transfer to yield a radical cation intermediate, in which the non-aromatic dithiole group is converted into an aromatic dithiolium ion. The radical moiety then dimerizes to form a TTFV dication [2] 2+ . Such oxidative dimerization reactivity has been widely used as a synthetic tool in the preparation of various redox-active functional molecular/ macromolecular systems, including p-conjugated oligomers, 30 polymers, 5,[31][32][33][34] and shape-persistent macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular alkyne–dithiolium cycloaddition: a joint experimental and DFT mechanistic study

2017

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“…The strong π–π and S…S interactions of TTFs facilitate the formation of coplanar molecular structures. Thus, TTFs exhibit unique charge transport characteristics, enabling TTFs to be applied as a organic optoelectronic material in the superconductor, organic field effect transistor (OFET), and sensors fields . Hou et al reported that adding TTF units into conjugated polymers increased the dimensionality of charge transport because of improved electron mobility along the polymer backbone through π ‐conjugation.…”

Section: Introductionmentioning

confidence: 99%

Improvement in Power Conversion Efficiency and Performance of P3HT/PCBM Solar Cells Using Dithiafulvalene‐Based π‐Conjugated Oligomers

Yang

Wen

Huang

et al. 2014

Macro Chemistry & Physics

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The improvement in the power conversion efficiency (PCE) and performance of poly(3‐hexylthiophene) (P3HT)/[6,6]‐phenyl‐C61butyric acid methyl ester (PCBM) solar cells are reported by using dithiafulvalene (DTF)‐based conjugated oligomers ((poly[2‐(9H‐fluoren‐9‐ylidene)‐4,5‐bis(hexylthio)‐1,3‐dithiole‐ran‐(2,1,3‐benzothiadiazole)] (PTBT) and poly[2,7‐(9,9‐dihexylfluorene)‐ran‐(2‐(9H‐fluoren‐9‐ylidene)‐4,5‐bis(hexylthio)‐1,3dithiole]‐ran‐(2,1,3‐benzothiadiazole)] (PFTBT)) that contain a DTF unit, which serves as an electron‐rich donor, and a benzothiadiazole group, which serves as an electron‐deficient acceptor in the main chain. A P3HT/PCBM device with 5 wt% PTBT exhibits an efficiency of up to 1.78%, which is higher than that of a device composed only of a P3HT/PCBM blend (1.01%). Introducing 2 wt% PTBT into the P3HT/PCBM blend substantially increases the charge‐carrier mobility from 2.01 × 10−4 to 4.59 × 10−4 cm2 V−1s−1. The improvement of the PCE is attributed to improved charge transport in the device and an increased open‐circuit voltage, suggesting that blending PTBT increases the intermolecular interaction of the molecules. In addition, doping the oligomer in ambient atmospheric conditions enhances the stability of these devices.

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Functional Macromolecules with Electron-Donating Dithiafulvene Unit

Cited by 15 publications

References 105 publications

Functional polymers based on electron-donating TTF and derivatives

Functional polymers based on electron-donating TTF and derivatives

Intramolecular alkyne–dithiolium cycloaddition: a joint experimental and DFT mechanistic study

Improvement in Power Conversion Efficiency and Performance of P3HT/PCBM Solar Cells Using Dithiafulvalene‐Based π‐Conjugated Oligomers

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