Al3+-Ion-Triggered Conformational Isomerization of a Rhodamine B Derivative Evidenced by a Fluorescence Signal - A Crystallographic Proof

Sen, Buddhadeb and Pal, Siddhartha and Banerjee, Samya and Lohar, Somenath and Chattopadhyay, Pabitra (2015) Al3+-Ion-Triggered Conformational Isomerization of a Rhodamine B Derivative Evidenced by a Fluorescence Signal - A Crystallographic Proof. In: EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (8). pp. 1383-1389.

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Abstract

A newly designed rhodamine B anisaldehyde hydrazone exhibits Al3+-ion-induced cis (L) to trans (L) conformational isomerization with respect to the xanthene moiety through a rotation about a N-N bond; the isomerization is indicated by a detectable naked-eye color change and a turn-on red fluorescence in 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) buffer (EtOH/Water 1:9 v/v; pH 7.4) at 25 degrees C. In support of this observation, detailed spectroscopic and physicochemical studies along with density function theory (DFT) calculations have been performed. This cis-to-trans conformational isomerization is due to Al3+ ion coordination, which induces this visual color change and the turn-on fluorescence response. To strengthen our knowledge of the conformational isomerization, detailed structural characterizations of the cis and trans isomers in the solid state were performed by single-crystal X-ray diffraction. To the best of our knowledge, this is the first structural report of both cis and trans conformational isomers for this family of compounds. Moreover, this noncytotoxic probe could be used to image the accumulation of Al3+ ions in HeLa and MCF-7 cell lines.

Item Type:	Journal Article
Publication:	EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH
Additional Information:	Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Keywords:	Isomerization; Aluminum; Rhodamine derivatives; Structure elucidation; Fluorescence
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	24 Apr 2015 05:47
Last Modified:	24 Apr 2015 05:47
URI:	http://eprints.iisc.ac.in/id/eprint/51377

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