Highly emissive π-conjugated alkynylpyrene oligomers: Their synthesis and photophysical properties

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1530-1533

  Shimizu, Hisao ^a   Fujimoto, Kazuhisa ^a   Furusyo, Masaru ^b   Maeda, Hajime ^c   Nanai, Yasuaki ^c   Mizuno, Kazuhiko ^c   Inouye, Masahiko ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b SUMITOMO ELECTRIC INDUSTRIES LTD   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; MASS SPECTROMETRY; OXIDATION; QUANTUM THEORY; SYNTHESIS (CHEMICAL);

FLUORESCENCE QUANTUM YIELDS; MONOMERIC BUILDING BLOCKS; OLIGOMERIZATION; PHOTOPHYSICAL PROPERTIES;

OLIGOMERS;

ALKYNYL GROUP; COPPER; OLIGOMER; PYRENE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL ANALYSIS; FLUORESCENCE SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; ORGANIC CHEMISTRY; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33846999020     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061959t     Document Type: Article

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45. Computational modeling was performed by DFT calculation in order to examine the π-conjugation of the para-linked oligomers. The two OR groups on the benzene ring can exist in two conformers, syn and anti, against the pyrene plane of the oligomers. We assumed that the free rotation of the pyrene and benzene planes on the oligomers may influence the ζ-conjugation. The structures of the para-linked oligomers were simplified as 15-18 shown in Supporting Information to make geometry optimization uncomplicated. The ZPE difference between the syn and anti conformers was calculated to be ≤2.4 kJ/mol on the basis of B3LYP/6-31G(d) level optimized structure. Furthermore, rotational barriers were estimated based on RHF/3-21G(d) level optimized structure (data not shown). The rotational barriers were also very small (syn to anti, 12 kJ/mol; anti to syn, 3.1 kJ/mol), implying that the pyrene and benzene planes can easily rotate on the oligomers at room temperature.
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