Bithiophene-Imide-Based Polymeric Semiconductors for Field-Effect Transistors: Synthesis, Structure−Property Correlations, Charge Carrier Polarity, an

Synthesis and Characterization of Thiophene-Containing Naphthalene Diimide n-Type Copolymers for OFET Application

Christine K. Luscombe

Naphthalene diimide (NDI) copolymers are attractive n-type materials for use in organic electronic devices. Four highly soluble NDI polymers are presented—each differing only in the thiophene content comprising the material. Electron mobilities as high as 0.076 cm² V⁻¹ s⁻¹for the novel material PNDI-3Th are reported. Polymer crystallinity and general macromolecular order are shown to effectively improve by increasing the number of thiophene units within the polymer backbone. The structure−property relationship of NDI−thiophene copolymers is presented and discussed as it pertains to organic field effect transistor (OFET) performance.

Phenyl vs Alkyl Polythiophene: A Solar Cell Comparison Using a Vinazene Derivative as Acceptor

Chem. Mater., Article ASAP DOI: 10.1021/cm903067a

Synthesis and characterization of donor-bridge-acceptor alternating copolymers containing perylene diimide units and their application to photovoltaic

DOI: 10.1002/pola.23889

Solution-Processible n-Channel Organic Field-Effect Transistors Based on Dicyanomethylene-Substituted Terthienoquinoid Derivative

J. Am. Chem. Soc., 2007, 129 (38), pp 11684–11685

Pyrazine-Containing Acene-Type Molecular Ribbons with up to 16 Rectilinearly Arranged Fused Aromatic Rings

J. Am. Chem. Soc., 2008, 130 (26), pp 8297–8306

Recent Progress in n-Channel Organic Thin-Film Transistors

Recent progress in the performance and molecular design of n-channel semiconductors during the past five years is summarized. The limitations and practicable solutions for n-channel organic thin-film transistors (OTFTs) are dealt with from the viewpoint of OTFT constitution and geometry, molecular design, and thin-film growth conditions. Strategies for methodology are especially highlighted with an aim to investigate basic issues in this field.

Adv. Mater., January 14, 2010, DOI: 10.1002/adma.200901454

Article n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing Substituents, Crystal Packing, and Field-Effect Transistor Characterist

P1 films exhibit a very high degree of crystallinity and an electron mobility > 0.01 cm² V⁻¹ s⁻¹ with a current on−off ratio of 10⁷, which is remarkably independent of film-deposition conditions.

J. Am. Chem. Soc., 2008, 130 (30), pp 9679–9694

Phthalimide-Based Polymers for High Performance Organic Thin-Film Transistors

Org. Lett., 2008, 10 (23), pp 5333–5336

J. Am. Chem. Soc., 2009, 131 (21), pp 7206–7207

Chem. Commun., 2008, 6034 - 6036, DOI: 10.1039/b812489b

Macromol. Rapid Commun. 2008, 29, 1444–1448

J. Am. Chem. Soc., 2007, 129 (23), pp 7246–7247

A Robust Low Band Gap Processable n-Type Conducting Polymer Based on Poly(isothianaphthene)

Macromolecules, 2001, 34 (6), pp 1810–1816

Poly(Pyridinium Phenylene)s: Water-Soluble N-Type Polymers

J. Am. Chem. Soc., 2009, 131 (49), pp 17724–17725

Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transist

Nature 457, 679-686 (5 February 2009) | doi:10.1038/nature07727

J. Am. Chem. Soc., 2009, 131 (1), pp 8–9

A Novel n-Type Conjugated Polymer DOCN-PPV: Synthesis, Optical, and Electrochemical Properties

Macromolecules, 2006, 39 (26), pp 8889–8891

A Highly Conjugated p- and n-Type Polythiophenoazomethine: Synthesis, Spectroscopic, and Electrochemical Investigation

Macromolecules, 2007, 40 (6), pp 1792–1795

An Ambipolar Peryleneamidine Monoimide-Fused Polythiophene with Narrow Band Gap

The donor−acceptor system can be electropolymerized to generate a functionalized polythiophene with a band gap of 0.9 eV and with ambipolar characteristics showing high electroactivity in both the p- and the n-doping process.

Org. Lett., 2007, 9 (11), pp 2171–2174

Synthesis and Characterization of Electron-Deficient and Highly Soluble (Bis)Indenofluorene Building Blocks for n-Type Semiconducting Polymers

These derivatives exhibit optical band gaps of 1.83 to 2.44 eV and low LUMO energies of −3.24 to −4.30 eV, representing a promising new building block class for n-type polymeric electronic materials.

Org. Lett., 2008, 10 (7), pp 1385–1388

Synthesis and Absorption Spectra of n-Type Conjugated Polymers Based on Perylene Diimide

The onset reduction (n-doping) potentials of PDIV and PDITh are at -0.62 V and -0.66 V versus Ag/Ag⁺ respectively, which correspond to the electron affinities (EAs) of 4.09 eV for PDIV and 4.05 eV for PDITh.

Macromolecular Rapid Communications Volume 29 Issue 17, Pages 1444 - 1448

Low-Bandgap Pyrazine Polymers: Ladder-Type Connectivity by Intramolecular S···N(sp2) Interactions and Hydrogen Bonds

Macromolecules, 2009, 42 (7), pp 2309–2312

Design, Synthesis, and Characterization of Ladder-Type Molecules and Polymers. Air-Stable, Solution-Processable n-Channel and Ambipolar Semiconductors

The onset LUMO energy for carrier electron stabilization is estimated as −4.0 to −4.1 eV, indicating an overpotential of 0.9−1.0 eV.

J. Am. Chem. Soc., 2009, 131 (15), pp 5586–5608