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Observing Second‐Order Nonlinear Optical Properties by Symmetry Breaking in Centrosymmetric Furan‐Containing Oligoaryl Cyclophandienes
Author(s) -
Lin HsinChieh,
Hsu JuiHung,
Lee ChaoKuei,
Tai Oliver YungHui,
Wang ChinHsien,
Chou ChihMing,
Chen KuangYen,
Wu YiLin,
Luh TienYau
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902115
Subject(s) - furan , nonlinear optical , symmetry breaking , nonlinear system , resonance (particle physics) , crystallography , order (exchange) , chemistry , symmetry (geometry) , computational chemistry , chemical physics , physics , mathematics , atomic physics , quantum mechanics , organic chemistry , geometry , finance , economics
Centrosymmetric furan‐containing cyclophandienes 3 and 4 , synthesized by our furan annulation protocol, have been shown to exhibit extraordinarily large Stokes shifts and second‐order nonlinear optical β values. The β values for 3 and 4 measured at 1.32 μm are 208 and 530×10 −30 esu, respectively. The β values of 3 and 4 are similar to those of respective cyclophenes 1 a and 7 in which strong hyperpoarizable interactions between two twisted π‐systems (oligoaryl and bridging double bond) might take place. Symmetry breaking due to the resonance contribution (cf. 2 ) and the unique structural features of 3 and 4 has been used to account for this unusual photophysical behavior.