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Thermally Triggered Isomerization in a Naphthalene‐Based Acylhydrazone with Solid‐State Optical Nonlinearity Response
Author(s) -
Huang Miaoling,
Qiu Rongxing,
Pan Zhonghua,
Tian Dan,
Tao Yunwen,
Lin Jinqing,
Luo GengGeng
Publication year - 2020
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202000767
Subject(s) - chemistry , isomerization , acentric factor , naphthalene , crystallography , pyridine , crystal structure , solid state , second harmonic generation , crystal (programming language) , computational chemistry , medicinal chemistry , organic chemistry , catalysis , physics , computer science , optics , laser , programming language
Under the assistance of the state‐of‐the‐art meta‐dynamics simulations, in this contribution, we report a push‐pull‐type acylhydrazone 4 ( Z ) ([ Z )‐2‐(naphthalen‐2‐yloxy)‐ N' ‐(pyridine‐2‐ylmethylene)acetohydrazide] connecting an electron‐donating naphthalene ether group with an accepting pyridyl unit, which could be thermally converted to its configurational isomer 4 ( E ) ([ E )‐2‐(naphthalen‐2‐yloxy)‐ N' ‐(pyridine‐2‐ylmethylene)acetohydrazide]. The thermally triggered Z ‐to‐ E configurational isomerization not only involves up to five chemical bonds undergoing 180° rotation in the backbone of acylhydrazone, but changes the crystal packing symmetry from a centrosymmetric space group to a non‐centrosymmetric one. Most impressively, the acentric crystal arrangement of 4 ( E ) exhibits a second‐harmonic generation (SHG) active response, about 2.5 times than that of KH 2 PO 4 (KDP) standard.