The synthesis of novel (N-)acene-based cyclooligomers is reported. Glaser-Hay coupling of the bisethynylated monomers results in cyclodimers and cyclotrimers that are separable by column and gel-permeation chromatographies. For the diazatetracene, the use of sec-butyl-silylethynyl groups is necessary to achieve solubility. Diazatetracene-based cyclodimers and cyclotrimers were used as semiconductors in thin-film transistors. Although their optoelectronic properties are quite similar, their electron mobilities in proof-of-concept thin-film transistors differ by an order of magnitude.
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http://dx.doi.org/10.1002/chem.202103193 | DOI Listing |
Chemistry
November 2021
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
The synthesis of novel (N-)acene-based cyclooligomers is reported. Glaser-Hay coupling of the bisethynylated monomers results in cyclodimers and cyclotrimers that are separable by column and gel-permeation chromatographies. For the diazatetracene, the use of sec-butyl-silylethynyl groups is necessary to achieve solubility.
View Article and Find Full Text PDFChemistry
October 2017
Institute for Molecular Science, Myodaiji, Okazaki, 444-8787, Japan.
A new family of non-planar heterocyclic molecules consisting of carbazoles was created. A bowl-shaped cyclodimer, a flake-shaped cyclotrimer, a double-decker-ring-shaped cyclotetramer and a cyclohexamer were synthesized by Ni -mediated one-shot cyclo-oligomerization of 1,8-dibromocarbazole, and were named [n]cyclo-1,8-carbazolylenes (n=3,4,6). [3]Cyclo-1,8-carbazolylene was found to act as a trivalent tridentate ligand for heteroatoms (B, P, Si), giving flake-shaped complexes.
View Article and Find Full Text PDFChem Commun (Camb)
March 2016
Department of Chemistry, Indian Institute of Science Education and Research (IISER), Pune - 411008, Maharashtra, India.
Benzofused dipyrrins react with metal salt copper(II) acetate to predominantly yield a cyclodimer along with a cyclotrimer. N-confused monobenzo-dipyrrin cyclomerized to trioxo-expanded norrole 13a and an acyclic dimer 14 whereas doubly N-confused monobenzo and dibenzo-dipyrrins yielded aza-heptalene 15 and an acyclic dimer 16.
View Article and Find Full Text PDFInorg Chem
July 2008
Department of Chemistry, Pusan National University, Pusan 609-735, Korea.
The reaction of (COD)PdCl 2 (COD = 1,5-cyclooctadiene) with bis(3-pyridyl)methylphenylsilane (L) in acetone affords single crystals consisting of cyclodimers, [PdCl 2(L)] 2, whereas the reaction in a mixture of dichloromethane and ethanol yields amorphous spheres consisting of cyclotrimers, [PdCl 2(L)] 3. The interconversion and morphology control between the crystals and the microspheres can be explained by the difference in flexibility between the cyclodimer and cyclotrimer.
View Article and Find Full Text PDFInorg Chem
February 2008
Department of Chemistry and Center for Plastic Information Systems, Pusan National University, Pusan, Korea.
Stepwise modulation of the ring size of metallacyclic compounds via subtle ring-constraint effects has been established. The reactions of (COD)PdCl 2 with p- or m-psb ligand [COD = 1,5-cyclooctadiene; p-psb = 1,4-bis(dimethyl-4-pyridylsilyl)benzene; m-psb = 1,4-bis(dimethyl-3-pyridylsilyl)benzene] in a mixture of acetone and ethanol at room temperature produce the metallacyclodimers [PdCl 2( p- or m-psb)] 2. The cyclodimeric species of [PdCl 2( p-psb)] 2 at the boiling temperature or via the sonication of the chloroform solution is completely converted to the cyclotrimer [PdCl 2( p-psb)] 3.
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