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A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K.

ABSTRACT: The title compound, C(28)H(30)N(2)O(3)·C(9)H(10)O(5), is a well known red leuco complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate (rhodamine B base abbreviated to RBB, a leuco dye) with ethyl gallate (EG, developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [Chem. Lett. (2007 ▶), 36, 1010-1011]. We have found a new phase of the material with two discrete base/developer complexes (RBB-A/EG-A and RBB-B/EG-B) in the asymmetric unit at 93 K. There are no significant differences between the two developer mol-ecules EG-A and EG-B. The lactone ring of RBB is opened in each mol-ecule to form a zwitterionic structure. However, the xanthene system is almost flat in RBB-A (r.m.s. deviation 0.0234 Å) but is less so in RBB-B (r.m.s. deviation 0.1095 Å). Furthermore, the ethyl groups of the xanthene diethyl-amino substituents lie on the same side of the xanthene plane in RBB-A but on opposite sides in RBB-B. Dimeric dye/developer complexes are formed through inter- and intra-molecular O-H⋯O hydrogen bonds and are linked further into dimers by additional O-H⋯O hydrogen bonds involving either EG-A or EG-B developer mol-ecules.

SUBMITTER: Mizuguchi J

PROVIDER: S-EPMC2961781 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K.

Mizuguchi Jin J

Acta crystallographica. Section E, Structure reports online 20080607 Pt 7

The title compound, C(28)H(30)N(2)O(3)·C(9)H(10)O(5), is a well known red leuco complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate (rhodamine B base abbreviated to RBB, a leuco dye) with ethyl gallate (EG, developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [Chem. Lett. (2007 ▶), 36, 1010-1011]. We have found a new phase of the material with two discrete base/developer complexes (RBB-A/EG-A and RBB-B/E ...[more]

PMID: 21202875

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Project description:The ability to tune the behavior of temperature-responsive polymers and self-assembled nanostructures has attracted significant interest in recent years, particularly in regard to their use in biotechnological applications. Herein, well-defined poly(2-(diethylamino)ethyl methacrylate) (PDEAEMA)-based core-shell particles were prepared by RAFT-mediated emulsion polymerization, which displayed a lower-critical solution temperature (LCST) phase transition in aqueous media. The tertiary amine groups of PDEAEMA units were then utilized as functional handles to modify the core-forming block chemistry via a postpolymerization betainization approach for tuning both the cloud-point temperature (T CP) and flocculation temperature (T CFT) of these particles. In particular, four different sulfonate salts were explored aiming to investigate the effect of the carbon chain length and the presence of hydroxyl functionalities alongside the carbon spacer on the particle's thermoresponsiveness. In all cases, it was possible to regulate both T CP and T CFT of these nanoparticles upon varying the degree of betainization. Although T CP was found to be dependent on the type of betainization reagent utilized, it only significantly increased for particles betainized using sodium 3-chloro-2-hydroxy-1-propanesulfonate, while varying the aliphatic chain length of the sulfobetaine only provided limited temperature variation. In comparison, the onset of flocculation for betainized particles varied over a much broader temperature range when varying the degree of betainization with no real correlation identified between T CFT and the sulfobetaine structure. Moreover, experimental results were shown to partially correlate to computational oligomer hydrophobicity calculations. Overall, the innovative postpolymerization betainization approach utilizing various sulfonate salts reported herein provides a straightforward methodology for modifying the thermoresponsive behavior of soft polymeric particles with potential applications in drug delivery, sensing, and oil/lubricant viscosity modification.

Dataset Information

A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K.

Publications

A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K.

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