Issue 12, 2008

Varied charge-transfer complex crystals formed between diols and benzoquinone in the solid and solution states

Abstract

Co-grinding of crystals of diols (electron donor) and benzoquinone (BQ, electron acceptor), and in some cases with crystals of a third aromatic compound, produces charge transfer (CT) complex crystals in the solid state without going through an obvious amorphous state, followed by a change in colour and in powder X-ray diffraction patterns. A milling power above a threshold is required for the new CT complex crystal formation, however, in some cases simple mixing of pulverized crystals is good enough to initiate the transformation. On exposing the CT complex crystals to air, without any mechanochemical force, they revert to the starting diol crystals by losing sublimable BQ molecules, rearranging hydrogen bonds and establishing a three-dimensional periodicity. Remarkably, solid-state and conventional solution crystallization give different results, i.e., formation or non-formation of CT complex crystals, or formation of different crystals with different colours. The phenomenon is surprisingly frequent and all three two-component CT systems and six out of the nine three-component systems investigated, exhibit different crystallization behaviour. A quartet structure where two BQ molecules are sandwiched by two naphthols was formed in the crystal obtained from solid-state crystallization. A new triplet CT complex structure in which a BQ is sandwiched by a naphthol and a biphenyl is also reported.

Graphical abstract: Varied charge-transfer complex crystals formed between diols and benzoquinone in the solid and solution states

Supplementary files

Article information

Article type
Paper
Submitted
01 Jul 2008
Accepted
24 Sep 2008
First published
09 Oct 2008

CrystEngComm, 2008,10, 1881-1890

Varied charge-transfer complex crystals formed between diols and benzoquinone in the solid and solution states

R. Kuroda, T. Sato and Y. Imai, CrystEngComm, 2008, 10, 1881 DOI: 10.1039/B811141C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements