Water‐Soluble Pyrrolo[3, 2‐b]pyrroles: Synthesis, Luminescence and Two‐Photon Cellular Imaging Properties. Issue 3 (3rd February 2017)

• Record Type: Journal Article
• Authors: Santra, Mithun; Jun, Yong Woong; Bae, Juryang; Sarkar, Sourav; Choi, Wanuk; Gryko, Daniel T.; Ahn, Kyo Han
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 3(2017)
• Page Start: 278
• Page End: 281
• Publication Date: 2017-02-03
• Subjects: fluorescence -- imaging agents -- pyrrolo[3, 2-b]pyrrole -- solid-state structures -- water-soluble; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201600613
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Water‐soluble, quadrupolar (A‐π‐D‐π‐A) pyrrolo[3, 2‐ b ]pyrrole dyes have been prepared, and their photophysical properties, including solid‐state fluorescence, are characterized. Analysis of packing patterns of the para analogue in single crystal shows negligible π–π interactions between molecular planes in stacked layers, resulting in no fluorescence quenching in the aggregate state. One of the dyes is used for fluorescence imaging of cells by confocal and two‐photon microscopy, showing potential applicability of such dyes as bioimaging agents. Abstract : The future of bioimaging applications? A direct approach to synthesize water‐soluble, quadrupolar pyrrolo[3, 2‐ b ]pyrrole dyes has been developed, where pyridinium moieties conjugated to the pyrrolopyrrole core act both as electron acceptors and water‐soluble groups. The new dyes show different emission behaviors as well as solid‐state luminescence. The packing pattern of the para analogue as a single crystal shows negligible π–π orbital interactions between linearly conjugated molecular planes in stacked layers. The para analogue stains cells under both one‐ and two‐photon excitation conditions for the first time.