Modular Fluorescent Benzobis(imidazolium) Salts: Syntheses, Photophysical Analyses, and Applications
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- 作者：Andrew J. Boydston ; Peter D. Vu ; Olga L. Dykhno ; Vicki Chang ; Alvin R. Wyatt ; II ; Adam S. Stockett ; Eric T. Ritschdorff ; Jason B. Shear ; Christopher W. Bielawski
- 刊名：Journal of the American Chemical Society
- 出版年：2008
- 出版时间：March 12, 2008
- 年：2008
- 卷：130
- 期：10
- 页码：3143 - 3156
- 全文大小：1534K
- 年卷期：v.130,no.10(March 12, 2008)
- ISSN：1520-5126
文摘
A series of benzobis(imidazolium) (BBI) salts has been prepared and studied as a new class ofversatile fluorescent materials. Using a high yielding, modular synthetic strategy, BBI salts with a range offunctionality poised for investigating fundamental and applications-oriented characteristics, including emissionwavelength tunability, solvatochromism, red-edge excitation, chemical stability, multiphoton excitation, andprotein conjugation, were prepared in overall yields of 40-97%. Through structural variation, the BBIsexhibited 
da.gif" BORDER=0 >em ranging between 329 and 561 nm while displaying 
fs up to 0.91. In addition, the emissioncharacteristics of these salts were found to exhibit strong solvent dependencies with Stokes shifts rangingfrom 4570 to 13 793 cm-1, depending on the nature of the BBI core. Although red-edge effects for BBIsalts with Br and BF4 counterions were found to be similar, unique characteristics were displayed by ananalogue with MeSO4 anions. The stability of an amphiphilic BBI was quantified in aqueous solutions ofvarying pH, and >85% of the emission intensity was retained after 2 h at pH 3-9. Through multiphotonexcitation experiments in aqueous solutions, a BBI salt was found to exhibit three-photon fluorescenceaction cross sections similar to serotonin. The application of BBI salts as fluorescent protein tags wasdemonstrated by conjugating bovine serum albumin to a maleimide-functionalized derivative.
da.gif" BORDER=0 >em ranging between 329 and 561 nm while displaying fs up to 0.91. In addition, the emissioncharacteristics of these salts were found to exhibit strong solvent dependencies with Stokes shifts rangingfrom 4570 to 13 793 cm-1, depending on the nature of the BBI core. Although red-edge effects for BBIsalts with Br and BF4 counterions were found to be similar, unique characteristics were displayed by ananalogue with MeSO4 anions. The stability of an amphiphilic BBI was quantified in aqueous solutions ofvarying pH, and >85% of the emission intensity was retained after 2 h at pH 3-9. Through multiphotonexcitation experiments in aqueous solutions, a BBI salt was found to exhibit three-photon fluorescenceaction cross sections similar to serotonin. The application of BBI salts as fluorescent protein tags wasdemonstrated by conjugating bovine serum albumin to a maleimide-functionalized derivative.