Highly efficient one-pot synthesis of α-free pyrylium salts with tunable fluorescence emission via ring-expanding reaction of triarylcyclopentadienes

被引：18
作者：
Yang, Lijian
Ye, Junwei [1 ]
Gao, Yuan
Deng, Dai
Gong, Weitao
Lin, Yuan
Ning, Guiling
机构：
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 23期
基金：
中国国家自然科学基金;
关键词：
alpha-Free pyrylium perchlorates; Fluorescence; Crystal structure; DFT calculation; SOLVATOCHROMISM; OXIDATION; DYNAMICS; ALCOHOLS;
D O I：
10.1016/j.tetlet.2013.03.113
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of a-free pyrylium perchlorates were prepared by one-pot oxidation of substituted cyclopentadiene derivatives in the presence of perchloric acid. A tunable fluorescence with green to red emission in dichloromethane and green to orange emission in the solid state can be achieved by changing the aryl groups on 2- or 4-position of pyrylium ring. Furthermore, single crystal structures and quantum chemistry calculation were conducted to understand the relationship between structures and optical properties. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2967 / 2971
页数：5
相关论文
共 35 条
  • [1] MOLECULAR DESIGN OF HOLE TRANSPORT MATERIALS FOR OBTAINING HIGH DURABILITY IN ORGANIC ELECTROLUMINESCENT DIODES
    ADACHI, C
    NAGAI, K
    TAMOTO, N
    [J]. APPLIED PHYSICS LETTERS, 1995, 66 (20) : 2679 - 2681
  • [2] Methylenepyran unsaturated Fischer carbene complexes from γ-methylpyrylium salts and alkynylcarbenes. Evolution to spiro-pyran-cyclopentenone compounds
    Ba, Fatou
    Le Poul, Pascal
    Robin-Le Guen, Francoise
    Cabon, Nolwenn
    Caro, Bertrand
    [J]. TETRAHEDRON LETTERS, 2010, 51 (04) : 605 - 608
  • [3] Synthesis, structural characterization, solvatochromism, and ion-binding studies of a ditopic receptor based on 2-(4-[2,2′: 6′,2"]terpyridin-4′-yl-phenyl)-1H-phenanthro[9,10-d] imidazole (tpy-HImzphen) unit
    Bhaumik, Chanchal
    Maity, Dinesh
    Das, Shyamal
    Baitalik, Sujoy
    [J]. RSC ADVANCES, 2012, 2 (06) : 2581 - 2594
  • [4] Solvatochromic investigation of highly fluorescent 2-aminobithiophene derivatives
    Bolduc, Andreanne
    Dong, Yanmei
    Guerin, Amelie
    Skene, W. G.
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2012, 14 (19) : 6946 - 6956
  • [5] The role of aromatic radical cations and benzylic cations in the 2,4,6-triphenylpyrylium tetrafluoroborate photosensitized oxidation of ring-methoxylated benzyl alcohols in CH2Cl2 solution
    Branchi, B
    Bietti, M
    Ercolani, G
    Izquierdo, MA
    Miranda, MA
    Stella, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) : 8874 - 8885
  • [6] Single crystals of the disubstituted anthracene 9,10-(Ph2P=S)2C14H8 selectively and reversibly detect toluene by solid-state fluorescence emission
    Fei, ZF
    Kocher, N
    Mohrschladt, CJ
    Ihmels, H
    Stalke, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (07) : 783 - 787
  • [7] Fischer, 1982, PYRYLIUM SALTS SYNTH
  • [8] Frisch M. J., 2003, Gaussian 03
  • [9] Many-photon dynamics of photobleaching
    Gavrilyuk, S.
    Polyutov, S.
    Jha, P. C.
    Rinkevicius, Z.
    Agren, H.
    Gei'mukhanov, F.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (47) : 11961 - 11975
  • [10] A facile oxidation and oxygen insertion of the cyclopentadiene ring by molecular oxygen in solution
    Gong, WT
    Ning, GL
    Li, XC
    Wang, L
    Lin, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) : 5768 - 5770
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