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Oxygen‐ and Sulfur‐bridged L‐shaped π‐Conjugated Molecules: Synthesis, Aggregated Structures, and Charge Transporting Behavior
Author(s) -
Okamoto Toshihiro,
Dosei Hiroaki,
Mitani Masato,
Murata Yoshinori,
Ishii Hiroyuki,
Nakamura Kenichi,
Yamagishi Masakazu,
Yano Masafumi,
Takeya Jun
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800403
Subject(s) - chemistry , conjugated system , sulfur , oxygen , molecule , charge (physics) , oxygen atom , polymer chemistry , organic chemistry , polymer , physics , quantum mechanics
A series of oxygen‐ and sulfur‐bridged L‐shaped π‐electron cores (π‐cores) with C s symmetry, dinaphtho [2, 1‐ b :2′,3′‐ d ] furan ( DNF−L ) and dinaphtho [2, 1‐ b :2′,3′‐ d ] thiophene ( DNT−L ), have been designed and investigated. DNF−L and DNT−L were successfully synthesized from commercially available 2‐methoxylnaphthalene in three and four steps, respectively. Notably, these compounds exhibited extremely high solubility in common organic solvents even without substituents and excellent thermal and chemical stability. X‐ray single‐crystal structural analyses of DNF−L and DNT−L reveal that both molecules form herringbone‐type packing structures suitable for two‐dimensional charge transport, but the packing of DNT−L has a large displacement in the direction of the longitudinal axis. Moreover, DNF−L shows a charge carrier mobility of up to 1.5 cm 2 /Vs in single‐crystal transistors, indicating that these L‐shaped molecules have excellent potential as organic semiconducting backbones with high solubility and high thermal and chemical stabilities.