The change of hydrogen position on π-conjugated bridge to affect NLO property of D(–NH2)-π(DHTPs)-A(–NO2) system

[Display omitted] •Based on the π-conjugated DHTPs, four isomers (1–4) with D(–NH2)-π(DHTPs)-A(–NO2) framework are designed and characterized.•The change of hydrogen position on DHTPs bridge can affect their nonlinear optics (NLO) property.•The change of hydrogen position on DHTPs brings distinctive...

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Veröffentlicht in:Computational and theoretical chemistry 2023-02, Vol.1220, p.114004, Article 114004
Hauptverfasser: Wang, Shuang-Rui, Yao, Yao, Su, Zhong-Min, Liu, Yan-Ling, Xu, Hong-Liang
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Sprache:eng
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Zusammenfassung:[Display omitted] •Based on the π-conjugated DHTPs, four isomers (1–4) with D(–NH2)-π(DHTPs)-A(–NO2) framework are designed and characterized.•The change of hydrogen position on DHTPs bridge can affect their nonlinear optics (NLO) property.•The change of hydrogen position on DHTPs brings distinctive changes in NICS, NPA charge, UV–vis absorption spectrum, etc. The donor-π-conjugated bridge-acceptor (D-π-A) is a classical framework to design high-performance organic electro-optical materials. In this work, based on the π-conjugated dihydrotetraazapentacenes (DHTPs), four isomers (1–4) with D(–NH2)-π(DHTPs)-A(–NO2) framework are designed and characterized. The 2 and 3 originate from single-hydrogen migration of 1, and 4 derives from double-hydrogen migration of 1. Significantly, the change of hydrogen position on DHTPs bridge can affect their nonlinear optics (NLO) property. Compared with the first hyperpolarizability (βtot) (4.08 × 103a.u.) of 1, the 6.90 × 103-2.56 × 104 a.u. of 2–4 are enhanced. More interestingly, the 4 has largest βtot value of 2.56 × 104, which is approximately equal to the sum of 6.90 × 103 a.u. of 2 and 1.82 × 104 a.u. of 3. Furthermore, the change of hydrogen position on DHTPs brings some distinctive changes in their geometric structure, nucleus-independent chemical shifts (NICS) value, natural population analysis (NPA) charge, UV–vis absorption spectrum along with its other electronic property that might be beneficial to explore their structure–property relationships.
ISSN:2210-271X
DOI:10.1016/j.comptc.2022.114004