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Zeng Z, Lee S, Son M, et al. Push-Pull Type Oligo(N-annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties. J Am Chem Soc. 2015;137(26):8572-83doi: 10.1021/jacs.5b04156.
Zeng, Z., Lee, S., Son, M., Fukuda, K., Burrezo, P. M., Zhu, X., Qi, Q., Li, R. W., Navarrete, J. T., Ding, J., Casado, J., Nakano, M., Kim, D., & Wu, J. (2015). Push-Pull Type Oligo(N-annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties. Journal of the American Chemical Society, 137(26), 8572-83. https://doi.org/10.1021/jacs.5b04156
Zeng, Zebing, et al. "Push-Pull Type Oligo(N-annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties." Journal of the American Chemical Society vol. 137,26 (2015): 8572-83. doi: https://doi.org/10.1021/jacs.5b04156
Zeng Z, Lee S, Son M, Fukuda K, Burrezo PM, Zhu X, Qi Q, Li RW, Navarrete JT, Ding J, Casado J, Nakano M, Kim D, Wu J. Push-Pull Type Oligo(N-annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties. J Am Chem Soc. 2015 Jul 08;137(26):8572-83. doi: 10.1021/jacs.5b04156. Epub 2015 Jun 25. PMID: 26062868.
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J Am Chem Soc. 2015 Jul 08;137(26):8572-83. doi: 10.1021/jacs.5b04156. Epub 2015 Jun 25.

Push-Pull Type Oligo(N-annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties.

Journal of the American Chemical Society

Zebing Zeng, Sangsu Lee, Minjung Son, Kotaro Fukuda, Paula Mayorga Burrezo, Xiaojian Zhu, Qingbiao Qi, Run-Wei Li, Juan T López Navarrete, Jun Ding, Juan Casado, Masayoshi Nakano, Dongho Kim, Jishan Wu

Affiliations

  1. †Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
  2. ‡State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China.
  3. §Spectroscopy Laboratory for Functional ?-Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120-749, Korea.
  4. ?Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan.
  5. ?Department of Physical Chemistry, University of Málaga, Campus de Teatinos s/n, 229071 Málaga, Spain.
  6. #Key Laboratory of Magnetic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, People's Republic of China.

PMID: 26062868 DOI: 10.1021/jacs.5b04156

Abstract

Research on stable open-shell singlet diradicaloids recently became a hot topic because of their unique optical, electronic, and magnetic properties and promising applications in materials science. So far, most reported singlet diradicaloid molecules have a symmetric structure, while asymmetric diradicaloids with an additional contribution of a dipolar zwitterionic form to the ground state were rarely studied. In this Article, a series of new push-pull type oligo(N-annulated perylene)quinodimethanes were synthesized. Their chain length and solvent-dependent ground states and physical properties were systematically investigated by various experimental methods such as steady-state and transient absorption, two-photon absorption, X-ray crystallographic analysis, electron spin resonance, superconducting quantum interference device, Raman spectroscopy, and electrochemistry. It was found that with extension of the chain length, the diradical character increases while the contribution of the zwitterionic form to the ground state becomes smaller. Because of the intramolecular charge transfer character, the physical properties of this push-pull system showed solvent dependence. In addition, density functional theory calculations on the diradical character and Hirshfeld charge were conducted to understand the chain length and solvent dependence of both symmetric and asymmetric systems. Our studies provided a comprehensive understanding on the fundamental structure- and environment-property relationships in the new asymmetric diradicaloid systems.

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