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Pyridazine‐Containing Diazatwistanthracene and Tetraazatwisttetracene: Synthesis, Crystal Structures and Third Order Non‐linear Optical Properties
Author(s) -
Fan Mingxuan,
Shen Yuqiang,
Zheng Yusen,
Yu Xianglin,
Li Miao,
Xu Liang,
Wang Jiapei,
Yang Li,
Li Junbo
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201804065
Subject(s) - pyridazine , phthalazine , chemistry , dihedral angle , absorption (acoustics) , crystallography , fluorescence , two photon absorption , molecule , pyrene , stereochemistry , medicinal chemistry , organic chemistry , hydrogen bond , optics , physics , laser
In this paper, two pyridazine‐heterocycles‐containing azaacenes 9,12‐diphenylphenanthro[4,5‐fgh]phthalazine ( DPPA ) and 2,9‐di‐tert‐butyl‐4,7,11,14‐tetraphenylpyridazino[4′,5′:9,10]phenanthro[4,5‐fgh]phthalazine ( TPPA ) have been synthesized and fully characterized. The single crystal analysis of TPPA showed that TPPA molecule exhibits a twisted structure with the dihedral angel of 27 ° between pyrene and pyridazine unit, which suppresses the π‐π stackings in the solid state. The two‐photon absorption properties of DPPA and TPPA were investigated, respectively, by using the femtosecond Z‐scan technique. The results showed that both DPPA and TPPA showed moderate two‐photon absorption cross‐section values, and the larger one was found to be 454 GM with TPPA . Obviously, the introduction of pyridazine ring into the skeleton of acenes forming a A−D‐A structure could lead to a much larger two‐photon absorption coefficient and two‐photon absorption cross section.