The synthesis and electronic absorption spectra of 3-phenyl-3(4-pyrrolidino-2-substituted phenyl)-3H-naphtho[2,1-b]pyrans:: further exploration of the ortho substituent effect

被引:33
|
作者
Gabbutt, CD [1 ]
Heron, BM [1 ]
Instone, AC [1 ]
机构
[1] Univ Leeds, Dept Colour & Polymer Chem, Leeds LS2 9JT, W Yorkshire, England
关键词
naphthopyrans; photochromism; steric effects; dual absorption hands; synthesis;
D O I
10.1016/j.tet.2005.09.143
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Introduction of a substituent into a sterically demanding 2-position of a 3-(4-pyrrolidinophenyl) ring of a 3,3-diaryl-3H-naphtho[2,1-b]pyran results in the generation of an additional short wavelength absorption band leading to organic photochromes that appear as dull shades of orange and red. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:737 / 745
页数:9
相关论文
共 50 条
  • [21] Photomodulable materials.: Synthesis and properties of photochromic 3H-naphtho[2,1-b]pyrans linked to thiophene units via an acetylenic junction
    Frigoli, M
    Moustrou, C
    Samat, A
    Guglielmetti, R
    HELVETICA CHIMICA ACTA, 2000, 83 (11) : 3043 - 3052
  • [22] Ring-opened Crystal Structure and Photochromism of 2,2-Bis(4-tertiary butyl phenyl)-3H-naphtho[2,1-b]pyran
    谈廷风
    庞美丽
    吴边鹏
    Chinese Journal of Structural Chemistry, 2009, 28 (02) : 187 - 190
  • [23] Ring-opened Crystal Structure and Photochromism of 2,2-Bis(4-tertiary butyl phenyl)-3H-naphtho[2,1-b]pyran
    谈廷风
    庞美丽
    吴边鹏
    结构化学, 2009, 28 (02) : 187 - 190
  • [24] 1H and 13C NMR chemical shift assignment of some 3H-naphtho[2,1-b]pyrans
    Demadrille, R
    Moustrou, C
    Campredon, M
    Giusti, G
    Faure, R
    MAGNETIC RESONANCE IN CHEMISTRY, 1999, 37 (04) : 328 - 330
  • [25] Ring-opened Crystal Structure and Photochromism of 2,2-Bis(4-tertiary butyl phenyl)-3H-naphtho[2,1-b]pyran
    Tan Ting-Feng
    Pang Mei-Li
    Wu Bian-Peng
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2009, 28 (02) : 187 - 190
  • [26] Control of the fading properties of photochromic 3,3-diaryl-3H-naphtho[2,1-b]pyrans
    Gabbutt, CD
    Heron, BM
    Instone, AC
    HETEROCYCLES, 2003, 60 (04) : 843 - 855
  • [27] SYNTHESE HOHER ANELLIERTER BENZO- UND 3H-NAPHTHO[2,1-B]PYRANE
    SCHIELE, C
    RUCH, M
    TETRAHEDRON LETTERS, 1966, (37) : 4413 - &
  • [28] 2′-Ethoxy-1,3,3-trimethylspiro[indoline-2,3′-3H-naphtho[2,1-b][1,4]oxazine]
    Lin, Jian
    Chai, Wenxiang
    Yang, Yunyun
    He, Jiaojiao
    Shu, Kangying
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1695 - U500
  • [29] SYNTHESIS OF 1'-METHYLSPIRO[3H-NAPHTHO[2,1-B]-PYRAN-3,2'(1,2-DIHYDROQUINOLINE)]
    SCHIELE, C
    KALINOWS.HO
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) : 416 - &
  • [30] Unusual stability of thermally induced colored isomers of photochromic 3-aryl-3-(1-naphthyl)-3H-naphtho[2,1-b]pyrans in solid state
    Guo, Kunpeng
    Cheng, Jun
    Liang, Xiaozhong
    Cao, Yaxiong
    Chu, Boyang
    Liu, Xuguang
    TETRAHEDRON LETTERS, 2015, 56 (25) : 3965 - 3968