- Highly Regioselective Domino Benzannulation Reaction of Buta-1,3-diynes To Construct Irregular Nanographenes
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The properties of nanographenes can be tuned by changing their shapes, therefore the development of new methods suitable for the synthesis of various nanographenes is highly desirable. Described herein is an intramolecular InCl3/AgNTf2-catalyzed regioselective domino benzannulation reaction of buta-1,3-diynes to build irregular nanographenes. Different nanographene compounds were easily obtained in moderate to high yields through careful design of the precursor compounds. This new domino reaction was successfully applied to a fourfold alkyne benzannulation of dimethoxy-1,1′-binaphthalene derivatives to arrive at novel chiral butterfly ligand precursors. The regioselectivity of the benzannulation reaction was unambiguously confirmed by X-ray crystallography. Moreover, this new method enables us to synthesize different nanographene isomers and study their optical properties as a function of shape.
- Yang, Wenlong,Bam, Radha,Catalano, Vincent J.,Chalifoux, Wesley A.
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- Chrysene-Based Blue Emitters
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Chrysene and its bisbenzannulated homologue, naphtho[2,3-c]tetraphene, were synthesized through a PtCl2-catalyzed cyclization of alkynes, which also furnished corresponding biaryls subsequent to a Glaser coupling reaction of the starting alkynes. The optoelectronic properties of 5,5′-bichrysenyl and 6,6′-binaphtho[2,3-c]tetraphene were compared to their chrysene-based “monomers”. Oxidative cyclodehydrogenations of bichrysenyl and its higher homologue towards large nanographenes were also investigated.
- Nathusius, Marvin,Ejlli, Barbara,Rominger, Frank,Freudenberg, Jan,Bunz, Uwe H. F.,Müllen, Klaus
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p. 15089 - 15093
(2020/10/21)
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- POLYCYCLIC AROMATIC COMPOUNDS AND METHODS FOR MAKING AND USING THE SAME
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Disclosed herein are embodiments of polycyclic aromatic compounds and methods of making and using the same. Various different types of polycyclic ring systems are disclosed, including, but not limited to, polymeric aromatic compounds (e.g., nanographene compounds), pentacene-like compounds, chiral aromatic compounds, asymmetric arene compounds formed from naphthalene-, anthracene-, phenanthrene-, and pyrene-based starting compounds, and dimerized aromatic compounds. Also disclosed herein are novel benzannulation-based methods for making the disclosed polycyclic aromatic compounds.
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Page/Page column 55; 56; 65
(2019/10/01)
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- 3,6,9,12-tetrasubstituted chrysenes: Synthesis, photophysical properties, and application as blue fluorescent OLED
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A short synthesis of unsubstituted chrysene is described to provide a cheap source of this compound. This chrysene was used to prepare 3,6,9,12- tetrabromochrysene, which was subsequently transformed into various 3,6,9,12-tetrasubstituted chrysenes bearing four aryl, alkynyl, or amino groups by means of the Suzuki, Sonogashira, or Buchwald-Hartwig coupling reaction, respectively. These substituents result in large bathochromic shifts in the chrysene absorption and emission spectra. These new chrysene derivatives show blue fluorescent emission (401-471 nm) with high quantum yields (0.44-0.87). DFT calculations on these chrysenes rationalize well the substituent effects on their HOMO and LUMO energy levels. One representative chrysene (6g) was used as a blue fluorescent emitter in an OLED device that showed an outstanding external quantum efficiency (η = 6.31%) with blue emission [CIE (x, y) = (0.13, 0.20)] and a low turn-on voltage (3.0 V).
- Wu, Tien-Lin,Chou, Ho-Hsiu,Huang, Pei-Yun,Cheng, Chien-Hong,Liu, Rai-Shung
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p. 267 - 274
(2014/01/17)
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