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

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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

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Publication details

The article was received on 10 Jan 2018, accepted on 30 Jan 2018 and first published on 30 Jan 2018


Article type: Paper
DOI: 10.1039/C8TC00145F
Citation: J. Mater. Chem. C, 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8TC00145F

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