174362-43-7Relevant academic research and scientific papers
Photochromism of Fulgides and Stereoelectronic Factors: Synthesis of (E)-4(3)-Adamantylidene-(5)-dicyanomethylene-3(4)-tetrahydrofuran-2-one 4 and 4a and (E)-4-adamantylidene-3-tetrahydrofuran-2,5-...
Sun, Zhiyuan,Hosmane, Ramachandra S.,Tadros, Maher,Guha, Shekhar,Chen, Wenpeng,Chen, Jar-Mo
, p. 1819 - 1828 (2007/10/03)
In the search for fulgides with potential semiconductor laser compatibitity, 4-adamantylidene-5-dicyanomethylene-3-tetrahydrofuran-2-one (4), along with its regioisomer 4a, have been synthesized from the corresponding fulgide 6 containing a succinic anhydride ring by reaction with malononitrile in the presence of diethylamine.Upon irradiation with a uv light at λmax 350 nm, a mixture of 4 and 4a revealed a considerably enhanced bathochromic shift to the visible region , λmax 605 nm as compared with the starting fulgide 6 which, upon analogous uv irradiation, absorbed at λmax 515 nm.In the search for semiconductor-laser-compatible fulgides with increased efficiency for the reverse bleaching reaction, another fulgide (E)-4-adamantylidene-3-tetrahydrofuran-2,5-dione (10) was synthesized in seven steps starting from 2-bromo-m-xylene.However, 10 failed to undergo electrocyclic ring-closure upon irradiation with a uv light at λmax 350 nm.The analogous fulgide 8, which contains an isopropylidene functionality in place of the adamantyl group of 10, was resynthesized for comparison, and showed two absorption maxima, one at 545 nm and the other at 620 nm.The missing physico-chemical data for 8 have also been provided.
