Steric effects on [4+4]-photocycloaddition reactions between complementary anthracene derivatives

被引:5
|
作者
Bailey, David [1 ]
Seifi, Nasim [1 ]
Williams, Vance E. [1 ]
机构
[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
关键词
Anthracene; Photodimer; Photoswitch; 4+4]-photocycloaddition; CROSS-LINKING; PHOTODIMERIZATION; PHOTOCYCLOADDITION; TEMPLATE; DIMER;
D O I
10.1016/j.dyepig.2010.05.016
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The steric effect of peripheral functional groups on the [4+4]-photocycloaddition between substituted anthracene derivatives was examined. The reactivity of 2,3,6,7-tetraphenylanthracene (IPA) with 2-phenylanthracene (PA), 2,9,10-trimethylanthracene (TMA) and 9,10-dimethyl-2,3-diphenylanthracene (DMDPA) was investigated. In all cases, the photodimers were formed in high yield despite the steric bulk of the peripheral substituents. It was further shown that although PA is capable of forming its homodimer, it selectively reacts with TPA when the latter is excited at 301 nm. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:313 / 318
页数:6
相关论文
共 50 条
  • [41] Fusicoccin synthesis by intramolecular [4+4] photocycloaddition of 2-pyridones: Stereocontrol of the cycloaddition and elaboration of the pentacyclic product
    McGee Jr., K.F.
    Al-Tel, T.H.
    Sieburth, S.McN.
    Synthesis, 2001, (08) : 1185 - 1196
  • [42] STERIC EFFECTS ON MESOMERISM .4. STERIC EFFECTS ON MESOMERISM IN DERIVATIVES OF ORTHO-NITRO-ACETANILIDE
    WEPSTER, BM
    VERKADE, PE
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1949, 68 (02): : 88 - 110
  • [43] UV-Light Responsive and Self-Healable Ethylene/Propylene Copolymer Rubbers Based on Reversible [4+4] Cycloaddition of Anthracene Derivatives
    He Zongke
    Niu Hui
    Li Yang
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2020, 221 (12)
  • [45] Quantum Chemical Study on the High-Pressure Effect for [4+4] Retrocycloaddition of Anthracene Cyclophane Photodimer
    Fukuda, Ryoichi
    Nakatani, Kaho
    JOURNAL OF PHYSICAL CHEMISTRY C, 2019, 123 (07): : 4493 - 4501
  • [46] Synthesis and molecular structure of a head-to-tail [4+4] dimer of a hexa-substituted anthracene
    Choi, MTM
    Yang, QC
    Mak, TCW
    Ng, DKP
    JOURNAL OF CHEMICAL RESEARCH, 2002, (12) : 644 - 646
  • [47] STEREOCONTROL OF 2-PYRIDONE [4+4] PHOTOCYCLOADDITION - A THERMAL-PHOTOCHEMICAL CYCLE TO PRODUCE EXCLUSIVELY TRANS CYCLOADDUCTS
    SIEBURTH, SM
    LIN, CH
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13): : 3597 - 3599
  • [48] Diastereoselective intramolecular [4 + 4] photocycloaddition reaction of N-(naphthylcarbonyl)anthracene-9-carboxamides: Temperature effects and reversal of diastereoselectivity
    Kohmoto, Shigeo
    Masu, Hyuma
    Tatsuno, Chuya
    Kishikawa, Keiki
    Yamamoto, Makoto
    Yamaguchi, Kentaro
    Journal of the Chemical Society, Perkin Transactions 1, 2000, (24): : 4464 - 4468
  • [49] Solvent-dependent stereoselectivity of bis-5-pyridone [4+4] photocycloaddition is due to H-bonded dimers
    Sieburth, SM
    McGee, KF
    ORGANIC LETTERS, 1999, 1 (11) : 1775 - 1777
  • [50] A water-soluble sunlight erasable ink based on [4+4] cycloaddition of 9-substituted anthracene
    Lu, Haipeng
    Wang, Xiang
    Zhou, Xianjing
    Zhang, Wei
    Wang, Xinping
    POLYMER CHEMISTRY, 2020, 11 (37) : 5992 - 5997