Please use this identifier to cite or link to this item:
Title: Pushing extended p-quinodimethanes to the limit: Stable tetracyano-oligo(N-annulated perylene)quinodimethanes with tunable ground states
Authors: Zeng, Z.
Ishida, M.
Zafra, J.L.
Zhu, X.
Sung, Y.M.
Bao, N. 
Webster, R.D.
Lee, B.S.
Li, R.-W.
Zeng, W.
Li, Y.
Chi, C. 
Navarrete, J.T.L.
Ding, J. 
Casado, J.
Kim, D.
Wu, J. 
Issue Date: 24-Apr-2013
Source: Zeng, Z., Ishida, M., Zafra, J.L., Zhu, X., Sung, Y.M., Bao, N., Webster, R.D., Lee, B.S., Li, R.-W., Zeng, W., Li, Y., Chi, C., Navarrete, J.T.L., Ding, J., Casado, J., Kim, D., Wu, J. (2013-04-24). Pushing extended p-quinodimethanes to the limit: Stable tetracyano-oligo(N-annulated perylene)quinodimethanes with tunable ground states. Journal of the American Chemical Society 135 (16) : 6363-6371. ScholarBank@NUS Repository.
Abstract: p-Quinodimethane (p-QDM) is a fundamental building block for the design of π-conjugated systems with low band gap and open-shell biradical character. However, synthesis of extended p-QDMs has usually suffered from their intrinsic high reactivity and poor solubility. In this work, benzannulation together with terminal cyano-substitution was demonstrated to be an efficient approach for the synthesis of a series of soluble and stable tetracyano-oligo(N-annulated perylene)quinodimethanes nPer-CN (n = 1-6), with the longest molecule having 12 para-linked benzenoid rings! The geometry and electronic structures of these oligomers were investigated by steady-state and transient absorption spectroscopy, nuclear magnetic resonance, electron spin resonance, superconducting quantum interference device, and FT Raman spectroscopy assisted by density functional theory calculations. They showed tunable ground states, varying from a closed-shell quinoidal structure for monomer, to a singlet biradical for dimer, trimer, and tetramer, and to a triplet biradical for pentamer and hexamer. Large two-photon absorption cross-section values were observed in the near-infrared range, which also exhibited a clear chain-length dependence. © 2013 American Chemical Society.
Source Title: Journal of the American Chemical Society
ISSN: 00027863
DOI: 10.1021/ja402467y
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.


checked on Mar 6, 2018


checked on Jan 23, 2018

Page view(s)

checked on Mar 11, 2018

Google ScholarTM



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.