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Pi-conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications

Weiping Wu1, Yunqi Liu, Daoben Zhu

  • 1Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.

Chemical Society Reviews
|April 27, 2010
PubMed

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Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
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Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Photochemical Electrocyclic Reactions: Stereochemistry

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Field-effect transistors (FETs) are integral to electronic circuits and distinguished by their three-terminal setup: the gate, drain, and source. These transistors operate as unipolar devices, which utilize either electrons or holes as charge carriers, in contrast to bipolar transistors, which use both types of carriers. The primary function of the FET is to modulate the flow of these carriers from the source to the drain through a channel. The voltage difference between the gate and source...