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Computational design of zinc-ion-responsive two-photon fluorescent probes with conjugated multi-structures

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Abstract

A series of conjugated multi-structured fluorescent probe molecules based on a salen ligand were designed and investigated in dimethyl sulfoxide solvent using a quantum-chemical method. The results indicate that the one-photon absorption and fluorescence emission spectra (λ O and λ EM) of these molecules generally show redshifts (of 23.1–74.5 and 22.7–116.6 nm, respectively) upon the coordination of the molecules to Zn2+. Large Stokes shifts (1511.2–11744.1 cm−1) were found for the molecules, meaning that interference between λ O and λ EM can be avoided for these molecules. The two-photon absorption spectra of the molecules usually present blueshifts, but the two-photon absorption cross-section (δ) greatly increases (by 221.5–868.0 GM) upon the coordination of the molecules with Zn2+. Most of the molecules show strong two-photon absorption peaks in the range 678.2–824.4 nm, i.e., in the near-infrared region. In a word, the expanded π-conjugated frameworks of these molecules lead to redshifted λ O and λ EM and enhanced δ values. Moreover, (L-phenyl)​2 and (L-phenyl-ethynyl)2 are the most suitable of the multi-structured molecules examined in this work for use as two-photon fluorescent probes for zinc ion detection in vivo.

Scheme of the calculated transition energies (E0k and E0n) and the transition dipole moments (M0k and Mkn). NTO 109, NTO 197 and NTO 228 of Zn(L-phenyl-ethynyl), Zn2(L-phenyl-ethynyl)2 and Zn3(L-phenyl)3 for one-photon  absorption, respectively.

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Acknowledgments

This work is supported by the Natural Science Foundation of China (grants 11404041, 21473071, 21173099, and 20973078), the Major State Basis Research Development Program (grant 2013CB 834801), the Natural Science Foundation of Jiangsu Provincial Department of Education (grant SCZ1212400003), Special Funding to Basic scientific Research Projects for Central Colleges, the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), the Foundation of State Key Laboratory of Theoretical and Computational Chemistry, Jilin University, State Key Laboratory of Satellite Ocean Environment Dynamics (Second Institute of Oceanography, SOA) (SOED1503), and the High Performance Computation Laboratory of Changzhou University.

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Authors and Affiliations

  1. School of Mathematics and Physics, Changzhou University, Changzhou, 213164, People’s Republic of China

    Shuang Huang & Xing-Fang Jiang

  2. State Key Laboratory of Satellite Ocean Environment Dynamics, Second Institute of Oceanography, Hangzhou, People’s Republic of China

    Shuang Huang & Xing-Fang Jiang

  3. School of Petrochemical Engineering, Changzhou University, Changzhou, 213164, People’s Republic of China

    Bao-Zhu Yang

  4. State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun, 130023, People’s Republic of China

    Ai-Min Ren

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Correspondence to Bao-Zhu Yang.

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Huang, S., Yang, BZ., Jiang, XF. et al. Computational design of zinc-ion-responsive two-photon fluorescent probes with conjugated multi-structures. J Mol Model 22, 34 (2016). https://doi.org/10.1007/s00894-015-2887-7

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