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Synthesis and non‐linear optical properties of new ionic species: tolan and diphenylbutadiyne with trimethylammonio and dimethylamino groups
Author(s) -
Umezawa Hirohito,
Okada Shuji,
Oikawa Hidetoshi,
Matsuda Hiro,
Nakanishi Hachiro
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.870
Subject(s) - chemistry , iodide , cationic polymerization , ionic bonding , methyl iodide , molecule , photochemistry , inorganic chemistry , medicinal chemistry , polymer chemistry , organic chemistry , ion
As new ionic organic species for second‐order non‐linear optical (NLO) materials, 4‐{[4‐(dimethylamino)phenyl]ethynyl}phenyltrimethylammonium iodide ( 1a ), 4‐{[4‐(dimethylamino)phenyl]butadiynyl}phenyltrimethylammonium iodide ( 2a ) and their derivatives with 4‐substituted benzensulfonate instead of iodide were successfully synthesized. The transparent wavelength region of 1a is wider than that of a typical NLO molecule, p ‐nitroaniline (pNA), whereas 2a and pNA have similar transparent regions. The experimental and calculated first hyperpolarizabilities (β) of 1a and 2a were found to be about 7 and 11 times, respectively, larger than those of pNA. Even when the volume factor was taken into account, the cationic part of 1a was found to be a better second‐order NLO material than pNA derivatives. Four second‐order NLO‐active crystals were found out of 12 salts synthesized. Copyright © 2004 John Wiley & Sons, Ltd.