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Indenofluorenes for organic optoelectronics: the dance of fused five- and six-membered rings enabling structural versatility
Abdullah Gul Univ, Turkey.
Linköping University, Department of Science and Technology, Laboratory of Organic Electronics. Linköping University, Faculty of Science & Engineering. Northwestern Univ, IL 60208 USA; Northwestern Univ, IL 60208 USA.
Abdullah Gul Univ, Turkey.
2022 (English)In: Journal of Materials Chemistry C, ISSN 2050-7526, E-ISSN 2050-7534, Vol. 10, no 22, p. 8496-8535Article, review/survey (Refereed) Published
Abstract [en]

Polycyclic pi-conjugated hydrocarbons (PCHs), either unfunctionalized or structurally modified derivatives, have attracted tremendous interest in the past few decades as high-performance semiconductors for use in new generations of organic (opto)electronic devices. Among several PCHs realized to date, the 6-5-6-5-6 pi-fused-ring backbone of indenofluorene (IF) stands out as a unique semiconducting architecture with great structural and property versatility affording six different regioisomers, diverse functionalization/substitution positions, pi-conjugation/delocalization patterns, aromatic behaviors, and electronic structures. In this review, we summarize and analyze the historical and recent advances in the design and implementation of IF-based semiconductors in organic transistor and solar cell devices, as well as in understanding the chemical structure-molecular property-semiconductivity relationships. Following an introduction to the fascinating properties of an IF pi-framework that distinguishes this core among PCHs, we present IF-based semiconductors and discuss their properties by classifying them into four main families (IF-diones, IF-DCVs/IF-TTFs, pi-IFs, and (un)substituted DH-IFs) considering whether methylene or methine C-bridges are present and how these positions are functionalized or substituted. For each family, design and synthetic approaches, molecular properties, and transistor/solar cell device applicability and/or performance are reviewed and discussed. At the end, we conclude with a section discussing the challenges and opportunities for future progress of IF-based semiconductor materials and related (opto)electronic technologies.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2022. Vol. 10, no 22, p. 8496-8535
National Category
Materials Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-185848DOI: 10.1039/d2tc00684gISI: 000802300500001OAI: oai:DiVA.org:liu-185848DiVA, id: diva2:1670888
Note

Funding Agencies|Turkish Academy of Sciences; AGU-BAP (Abdullah Gul University-Scientific Research Projects Funding Program) [FYL-2018-115, FYL-2016-65]; Scientific and Technological Research Council of Turkey [TUBITAK-113C021]; Science Academy through the Young Scientist Award Programs (TUBA-GEBIP-2015); Science Academy through the Young Scientist Award Programs (BAGEP-2014)

Available from: 2022-06-16 Created: 2022-06-16 Last updated: 2022-06-16

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Facchetti, Antonio
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