36288-06-9Relevant academic research and scientific papers
Halogenated (F, Cl, Br, or I) Diphenylhexatrienes: Crystal Structures, Fluorescence Spectroscopic Properties, and Quantum Chemical Calculations
Sonoda, Yoriko,Goto, Midori,Matsumoto, Yuki,Shimoi, Yukihiro,Sasaki, Fumio,Furube, Akihiro
, p. 4060 - 4071 (2016/07/19)
A series of halogenated compounds, (E,E,E)-1,6-di(4-X-phenyl)hexa-1,3,5-trienes (1: X = F, 2: X = Cl, 3: X = Br, 4: X = I), were synthesized and their crystal structures and fluorescence emission properties were systematically investigated. Single-crystal X-ray analysis reveals that molecules are arranged via X/X halogen bonds and/or CH/X-type hydrogen bonds to form a herringbone structure in 1 and π-stacked structures in 2-4. In the structures of 2 and 3, which are almost isomorphous, the distance and displacement for the nearest stacking molecules are smaller than those in 4. Although the structures of 2-4 are basically not greatly different from each other, the nearest-neighbor arrangements are π-stacked in 2 and 3, but herringbone in 4. Steady-state and time-resolved measurements show that the solid-state fluorescence properties also strongly depend on the halogen size. The fluorescence spectra are red-shifted and the Stokes shifts are large in 2 and 3 relative to those in 1 and 4, resulting from the difference in molecular arrangement in the crystal structure. The experimentally observed clear correlation between crystal structure and optical transition energy is reproduced fairly well by quantum chemical calculations for the excited states of molecular pairs in the X-ray determined structures of 1-4.
Preparation of p,p'-Disubstituted-α,ω-Diphenyl Polyenes
Spangler, Charles W.,McCoy, Ray K.,Dembek, Alexa A.,Sapochak, Linda S.,Gates, Bradley D.
, p. 151 - 154 (2007/10/02)
Condensation of appropriately substituted benzaldehydes or cinnamaldehydes with either bis-Wittig reagents or bis-phosphonate esters (Horner-Emmons-Wadsworth modifications) containing one or two double bond units are general and quite efficient preparatio
