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Issue 31, 2016
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Multi-functional supramolecular building blocks with hydroxy piperidino groups: new opportunities for developing nonlinear optical ionic crystals

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Abstract

We report on multi-functional supramolecular building blocks for obtaining a non-centrosymmetric crystal structure, which is the essential requirement for achieving a macroscopic second-order nonlinear optical activity. The supramolecular building blocks PM (piperidin-4-ylmethanol) and PO (piperidin-4-ol) consist of a piperidino group acting as a strong electron-donating group and a hydroxyl group acting as a strong hydrogen-bonding group, which also may act as a ‘site-isolation’ group. The quinolinium crystals PMQ-T and POQ-T that introduce PM and PO blocks, respectively, exhibit a non-centrosymmetric crystal structure with nonlinear optical activity, while analogous quinolinium DAQ-T crystal with the widely used N,N-dimethylamino (DA) group exhibits a centrosymmetric crystal structure without nonlinear optical activity. Compared to the DAQ-T crystal, the PMQ-T and POQ-T crystals exhibit a lower tendency to form a hydrate phase in the crystalline state. The PMQ-T crystal exhibits a higher molecular optical nonlinearity in the crystalline state than the DAQ-T crystal, which is attributed to the ‘site-isolation’ effect resulting from the bulky PM block. In addition, the PMQ-T crystal exhibits large macroscopic optical nonlinearities with more than 3 times higher off-diagonal effective hyperpolarizability than that of benchmark stilbazolium crystals. Therefore, multi-functional supramolecular building blocks PM and PO can give new opportunities for developing non-centrosymmetric ionic crystals for nonlinear optical applications.

Graphical abstract: Multi-functional supramolecular building blocks with hydroxy piperidino groups: new opportunities for developing nonlinear optical ionic crystals

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Supplementary files

Article information


Submitted
19 Feb 2016
Accepted
16 Jun 2016
First published
06 Jul 2016

CrystEngComm, 2016,18, 5832-5841
Article type
Paper

Multi-functional supramolecular building blocks with hydroxy piperidino groups: new opportunities for developing nonlinear optical ionic crystals

K. Lee, S. Lee, H. Yun, M. Jazbinsek, J. W. Kim, F. Rotermund and O. Kwon, CrystEngComm, 2016, 18, 5832
DOI: 10.1039/C6CE00401F

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