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Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Paper ID Volume ID Publish Year Pages File Format Full-Text
31443 44788 2014 21 PDF Available
Title
Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication
Abstract

•Synthesis and reactivity of α-diketone-type acene precursors are reviewed.•Preparation of large or functionalized acenes via α-diketones is overviewed.•The mechanism of photoinduced decarbonylation of α-diketones is discussed.•Fabrication of acene-based devices by the photoprecursor method is introduced.

Acenes are highly promising p-type organic semiconductors, and have been the subject of intense studies. However, acenes are often low in solubility and stability, which poses major obstacles in the synthesis and processing of this class of compounds. In order to overcome the problem, a series of α-diketone-type acene precursors have been developed. These precursors are generally more soluble and stable than the corresponding acene compounds, and their quantitative conversion can be achieved simply by photoirradiation both in solution and in the solid state. Further, the irreversible photoinduced removal of the α-diketone unit can be used to alter the optoelectronic properties of fluorophores. This review overviews the synthesis and photochemical properties of α-diketone-type acene precursors, as well as their use as intermediates in preparation of large acenes or highly functionalized acene derivatives. Computational studies on the mechanism of α-diketone photolysis and the use of α-diketone derivatives in fabrication of organic devices are also summarized in this review.

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Keywords
AFM, atomic force microscopy; BHJ, bulk heterojunction; CIS, configuration interaction singles; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DCB, o-dichlorobenzene; DIBAL, diisobutylaluminium hydride; DDQ, 2,3-dichloro-5,6-dicyanobenzoquinone; DFT, density fu
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Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology C: Photochemistry Reviews - Volume 18, March 2014, Pages 50–70
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us