Synthesis, crystal structure and non-linear optical properties of boronates derivatives of salicylideniminophenols

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• 作者：Blanca M. Muñ ; oz ; Rosa Santillan ; Mario Rodrí ; guez ; José ; Manuel Mé ; ndez ; Margarita Romero ; Norberto Farfá ; n ; Pascal G. Lacroix ; Keitaro Nakatani ; Gabriel Ramos-Ortí ; z ; Jos
• 关键词：Boronates ; NLO ; ¹¹B NMR ; X-ray
• 刊名：Journal of Organometallic Chemistry
• 出版年：2008
• 出版时间：1 April 2008
• 年：2008
• 卷：693
• 期：7
• 页码：1321-1334
• 全文大小：598 K

文摘

The condensation in one step of a series of salicylaldehydes and 2-amino-5-nitrophenol with 1-naphthylboronic acid, 2-naphthylboronic acid, and o-tolylboronic acid to give the corresponding boronates 1a–3a, 1b–3b and 1c–3d, is reported. The X-ray crystal structures of 1a, 2b and 3b allowed determining the - and β-angle between the stilbene skeleton and the aryl or naphthylboronic fragments; these values are indicative of different conformations for the aryl moieties around the (B–C) boron–carbon bond which could potentially modulate the electronic properties on the boron stilbene compounds. All compounds were characterized by ¹H, ¹¹B and ¹³C NMR spectroscopy, UV, IR and mass spectrometry. Second- and third-order non-linear optical characterizations were also performed by EFISH and THG Maker Fringe techniques, respectively. Compounds 3a–3d containing an –N(Et)₂ donor group gave the best NLO response in second- and third-order.