Tetracyanoquaterrylene and Tetracyanohexarylenequinodimethanes with Tunable Ground States and Strong Near-Infrared Absorption†
Dr. Zebing Zeng
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorSangsu Lee
Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Search for more papers by this authorJosé L. Zafra
Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Search for more papers by this authorDr. Masatoshi Ishida
Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Search for more papers by this authorXiaojian Zhu
Key Laboratory of Magnetic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201 (China)
Search for more papers by this authorZhe Sun
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorYong Ni
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorProf. Richard D. Webster
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore (Singapore)
Search for more papers by this authorProf. Run-Wei Li
Key Laboratory of Magnetic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201 (China)
Search for more papers by this authorCorresponding Author
Prof. Juan T. López Navarrete
Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Chunyan Chi
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Jun Ding
Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Juan Casado
Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dongho Kim
Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Jishan Wu
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Institute of Materials Research and Engineering, A*STAR, 3 Research Link, 117602, Singapore (Singapore)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorDr. Zebing Zeng
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorSangsu Lee
Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Search for more papers by this authorJosé L. Zafra
Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Search for more papers by this authorDr. Masatoshi Ishida
Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Search for more papers by this authorXiaojian Zhu
Key Laboratory of Magnetic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201 (China)
Search for more papers by this authorZhe Sun
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorYong Ni
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorProf. Richard D. Webster
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore (Singapore)
Search for more papers by this authorProf. Run-Wei Li
Key Laboratory of Magnetic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201 (China)
Search for more papers by this authorCorresponding Author
Prof. Juan T. López Navarrete
Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Chunyan Chi
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Jun Ding
Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Juan Casado
Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dongho Kim
Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Jishan Wu
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Institute of Materials Research and Engineering, A*STAR, 3 Research Link, 117602, Singapore (Singapore)
Juan T. López Navarrete, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Chunyan Chi, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Jun Ding, Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
Juan Casado, Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
Dongho Kim, Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
Jishan Wu, Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
Search for more papers by this authorJ.W. acknowledges the financial support from MOE Tier 2 grant (MOE2011-T2-2-130) and IMRE Core funding. The work at Yonsei Univ. was supported by WCU programs (R32-2010-10217-0) and an AFSOR/APARD grant (no. FA2386-09-1-4092). The work at Spain was supported by the Ministerio de Educación y Ciencia of Spain and by FEDER funds.
Graphical Abstract
Biradicaloids based on quinoidal rylenes! Soluble and stable tetracyanoquaterrylenequinodimethane (QR-CN) and tetracyanohexarylenequinodimethane (HR-CN) were synthesized. QR-CN has a closed-shell quinoidal structure in the ground state, whereas HR-CN has a singlet biradical ground state. Both compounds showed very strong one-photon and two-photon absorption in the NIR range.
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