Synthesis, Characterization, and Crystal Structure of the Lactone Form of Rhodamine B

Wang, Xiqing; Song, Mingjun; Long, Yingcai

doi:10.1006/jssc.2000.9002

Cited by 34 publications

(15 citation statements)

References 16 publications

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“…However, this distance agrees with the value found experimentally in solid Fluorescein [51], in some fluorescein derivatives [52], and in Rhodamines [53]. The analysis of the theoretical data suggests that the presence of the aromatic ring as a substituent increases the bond length of lactone due to steric factors.…”

Section: Analysis Of Neutral Nez and Nel Structures (Fh 2 )supporting

confidence: 85%

Protolytic fluorescein species evaluated using chemometry and DFT studies

et al. 2010

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Section: Analysis Of Neutral Nez and Nel Structures (Fh 2 )supporting

confidence: 85%

Protolytic fluorescein species evaluated using chemometry and DFT studies

et al. 2010

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“…The cross-linked analysis of the 2D rotating frame nuclear Overhauser effect spectroscopy (ROESY) spectrum ( Supporting Information File 1 , Figures S11, S12 and S13) and the DEPT-ed-HSQC spectrum ( Supporting Information File 1 , Figure S14) generates a set of information useful for the determination of the spatial position of the fluorophore with respect to the CD scaffolds and for the analysis of the preferred conformation assumed by Rho-β-CD in solution. These data, together with the results presented by Wang et al [ 25 ] about the crystal structure of rhodamine B in lactone form, allowed us to propose the model shown in Fig. 6 for the intermolecular inclusion mode of Rho-β-CD.…”

Section: Resultssupporting

confidence: 62%

“…The two additional cross peaks at 7.91 and 6.74 ppm are the result of the spatial interactions of the methyl units with the protons A and D of the aromatic ring adjacent to the spirolactam unit ( Supporting Information File 1 , Figure S3). Assuming that the spirolactam is positioned perpendicular to the plane described by the xanthene unit (as reported in [ 25 ]), then the aforementioned, two additional cross peaks are the result of intermolecular interactions (see models in Fig. 6 ).…”

Section: Resultsmentioning

confidence: 96%

New synthetic strategies for xanthene-dye-appended cyclodextrins

Darcsi¹,

Bálint²,

Benkovics³

et al. 2016

Beilstein J. Org. Chem.

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SummaryXanthene dyes can be appended to cyclodextrins via an ester or amide bridge in order to switch the fluorescence on or off. This is made possible through the formation of nonfluorescent lactones or lactams as the fluorophore can reversibly cyclize. In this context we report a green approach for the synthesis of switchable xanthene-dye-appended cyclodextrins based on the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). By using 6-monoamino-β-cyclodextrin and commercially available inexpensive dyes, we prepared rhodamine- and fluorescein-appended cyclodextrins. The compounds were characterized by NMR and IR spectroscopy and MS spectrometry, their UV–vis spectra were recorded at various pH, and their purity was determined by capillary electrophoresis. Two potential models for the supramolecular assembly of the xanthene-dye-appended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization.

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“…For background to phthalides as natural products, see: Pedrosa et al (2006). For a related structure, see: Wang et al (2001). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

“…1),there is an inversion center, which is located at the mid-point of C(8)-C(8 A) bond. All of the bond lengths and bond angles are in the normal ranges (Wang et al, 2001). In the crystal lattice,…”

Section: S1 Commentmentioning

confidence: 99%