Synthesis, size-dependent optoelectronic and charge transport properties of thieno(bis)imide end-substituted molecular semiconductors
| Autor: | Alberto Zanelli, Manuela Melucci, Filippo De Angelis, Massimo Gazzano, Margherita Durso, Massimiliano Cavallini, Raffaella Capelli, Michele Muccini, Cristian Bettini, M. Grazia Lobello, Stefano Toffanin, Viviana Biondo, Denis Gentili |
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| Rok vydání: | 2013 |
| Předmět: |
Materials Chemistry2506 Metals and Alloys
Materials science Pentamer Trimer 02 engineering and technology Structure-property relationships Field effect transistors Electroluminescence 010402 general chemistry 01 natural sciences Oligomer Structure–property relationships Biomaterials chemistry.chemical_compound Electronic Oligothiophenes Materials Chemistry Ambipolar charge transport Molecular semiconductors Electronic Optical and Magnetic Materials Chemistry (all) Condensed Matter Physics Electrical and Electronic Engineering Optical and Magnetic Materials Imide HOMO/LUMO Ambipolar diffusion business.industry General Chemistry 021001 nanoscience & nanotechnology 0104 chemical sciences Stille reaction chemistry Optoelectronics 0210 nano-technology business |
| Zdroj: | Organic electronics 14 (2013): 3089–3097. doi:10.1016/j.orgel.2013.07.019 info:cnr-pdr/source/autori:Margherita Durso (a); Cristian Bettini (b); Alberto Zanelli (a); Massimo Gazzano (a); M. Grazia Lobello (c); Filippo De Angelis (c); Viviana Biondo (d); Denis Gentili (e); Raffaella Capelli (e); Massimiliano Cavallini (e); Stefano Toffanin (e); Michele Muccini (d,e); Manuela Melucci (a)/titolo:Synthesis, size-dependent optoelectronic and charge transport properties of thieno(bis)imide end-substituted molecular semiconductors/doi:10.1016%2Fj.orgel.2013.07.019/rivista:Organic electronics (Print)/anno:2013/pagina_da:3089/pagina_a:3097/intervallo_pagine:3089–3097/volume:14 |
| ISSN: | 1566-1199 |
| Popis: | The synthesis of two new thieno(bis)imide (TBI, N) end functionalized oligothiophene semiconductors is reported. In particular, trimer (NT3N) and pentamer (NT5N) have been synthesized and characterized. Two different synthetic approaches for their preparation were tested and compared namely conventional Stille cross coupling and direct arylation reaction via C-H activation. Theoretical calculations, optical and electrochemical characterization allowed us to assess the role of the ?-conjugation extent, i.e., of the oligomer size on the optoelectronic properties of these materials. In both {TBI} ended compounds, due to the strong localization of the {LUMO} orbital on the {TBI} unit, the {LUMO} energy is almost insensitive to the oligomer size, this being crucial for the fine-tailoring of the energy and the distribution of the frontier orbitals. Surprisingly, despite its short size and contrarily to comparable TBI-free analogues, {NT3N} shows electron charge transport with mobility up to ?N = 10-4 cm2 V-1 s-1, while increasing the oligomer size to {NT5N} promotes ambipolar behavior and electroluminescence properties with mobility up to ?N = 0.14 cm2 V-1 s-1 and to ?P = 10-5 cm2 V-1 s-1. |
| Databáze: | OpenAIRE |
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