Issue 9, 2018

Two novel rhodamine-based molecules with different mechanochromic and photochromic properties in solid state

Abstract

Two novel molecules (An[double bond, length as m-dash]RhB-1 and An[double bond, length as m-dash]RhB-2) were synthesized using Rhodamine B and anthracene as building units via Schiff base chemistry with different spacers. This small structural variation led to a dramatic difference in mechanochromic and photochromic properties in the solid state. They both showed a force-induced color change. However, An[double bond, length as m-dash]RhB-1 not only displayed two color changes due to the ring-opening isomerization of the rhodamine derivatives, but also exhibited rarely reported photochromic properties. The photochromic behaviour of An[double bond, length as m-dash]RhB-1 resulted from its large free volume in the amorphous solid state and the relatively high stability of its zwitterionic species in its ring-open form. In contrast, An[double bond, length as m-dash]RhB-2 gave a tricolored switch upon force action but no photochromic behavior is observed. The three-color variations in this molecule originated from the transformation of the different physical packing modes of anthracene and force-triggered chemical reaction of Rhodamine B lactam. The Schiff base group for the molecular design of mechanochromic and photochromic materials can be extended to other systems, which may open a new strategy to provide a broad perspective for the development of multi-stimuli responsive materials.

Graphical abstract: Two novel rhodamine-based molecules with different mechanochromic and photochromic properties in solid state

Supplementary files

Article information

Article type
Paper
Submitted
10 Jan 2018
Accepted
30 Jan 2018
First published
30 Jan 2018

J. Mater. Chem. C, 2018,6, 2270-2274

Two novel rhodamine-based molecules with different mechanochromic and photochromic properties in solid state

Z. Ma, Y. Ji, Y. Lan, G. Kuang and X. Jia, J. Mater. Chem. C, 2018, 6, 2270 DOI: 10.1039/C8TC00145F

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