Photochromic Behaviour of Bis[4-(N,N-dimethylamino)phenyl]-substituted 3 H-Naphtho[2,1-b]pyran and 2 H-1-Benzopyran-Reference-Cited by-同舟云学术

Photochromic Behaviour of Bis[4-(N,N-dimethylamino)phenyl]-substituted 3 H-Naphtho[2,1-b]pyran and 2 H-1-Benzopyran

Published:1997-04 Issue:17 Volume:38 Page:3075-3078
ISSN:0040-4039
Container-title:Tetrahedron Letters
language:en
Short-container-title:Tetrahedron Letters

Author:

Harié Guénaëlle,Samat André,Guglielmetti Robert,De Keukeleire* Denis,Saeyens Wim,Van Parys Inge

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference14 articles.

1. For a review: Crano, J.C.; Kwak, W.S.; Welch, C.N, in: Ardle C.B. Applied Photochromic Polymer Systems, Chapman & Hall, New York, 1994.

2. 1: 62%, recryst. from hexane, mp: 158°C.1H NMR (250 MHz, CDCl3): δ (ppm): 6.26 (d, J = 9.9 Hz, 1H), 7.19 (d, J = 8.9 Hz, 1H), 7.23 (m, 2H), 7.29 (m, 1H), 7.30 (m, 4H), 7.31 (m, 1H), 7.44 (m, 1H), 7.48 (m, 4H), 7.65 (d, J = 8.6 Hz, 1H), 7.69 (d, J = 8.6 Hz, 1H), 7.94 (d, J = 8.5 Hz, 1H).13C-NMR (62.5 MHz, CDCl3): δ (ppm): 118.43, 119.60, 121.40, 123.68, 126.69, 127.10 (4C), 127.60 (2C), 127.79, 128.17 (4C), 128.59, 129.90. 2: 49%, purification by flash chromatography (Et2O), mp: 223°C.1H-NMR (250 MHz, CDCl3): δ (ppm): 2.90 (s, 12H), 6.66 (d, J = 8.8 Hz, 4H), 7.16 (d, J = 8.8 Hz, 1H), 7.22–7.27 (m, 2H), 7.33 (d, J = 8.8 Hz, 4H), 7.43 (m, 1H), 7.61 (d, J = 8.8 Hz, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.94 (d, J = 8.4 Hz, 1H).13C-NMR (62.5 MHz, CDCl3): δ (ppm): 40.84 (4 C), 112.21 (4C), 118.75, 118.88, 121.63, 123.54, 126.66, 128.38 (4C), 128.74, 128.94, 129.71. 3: 55%, purification by flash chromatography (hexane: CH2Cl2 1:1), mp: 144°C.1H-NMR (600 MHz, C6D6): δ (ppm): 2.93 (s, 12H), 6.12 (d, J = 9.8 Hz, 1H), 6.55 (d, J = 9.8 Hz, 1H), 6.68 (d, J = 8.9 Hz, 4H), 6.80 (dt, J = 7.4 Hz and 0.9 Hz, 1H), 6.89 (d, J = 7.9 Hz, 1H), 6.98 (dd, J = 7.4 Hz and 1.5 Hz, 1H), 7.10 (dt, J = 7.9 Hz and 1.5 Hz, 1H), 7.30 (d, J = 8.9 Hz, 4H).13C-NMR (150 MHz, C6D6): δ (ppm): 40.41 (4C), 111.82 (4C), 116.31, 120.49, 121.12, 122.18, 126.24, 127.91, 129.04 (4C).

3. Van Gemert, B.; Bergomi, M. (PPG Industries) U.S. Patent 1991, 5066 818.

4. Photochromism of Diarylnaphthopyrans

5. Heller, H.; Oliver, S.N.; Whittal, J.; Brettle, J.; Trundle, C.; Baskerville, M.W. (The Plessey Company) U.S. Patent 1989, 4818 096.

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