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Issue 8, 2017
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An unprecedented amplification of near-infrared emission in a Bodipy derived π-system by stress or gelation

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Abstract

We report an unprecedented strategy to generate and amplify near-infrared (NIR) emission in an organic chromophore by mechanical stress or gelation pathways. A greenish-yellow emitting film of π-extended Bodipy-1, obtained from n-decane, became orange-red upon mechanical shearing, with a 15-fold enhancement in NIR emission at 738 nm. Alternatively, a DMSO gel of Bodipy-1 exhibited a 7-fold enhancement in NIR emission at 748 nm with a change in emission color from yellow to orange-red upon drying. The reason for the amplified NIR emission in both cases is established from the difference in chromophore packing, by single crystal analysis of a model compound (Bodipy-2), which also exhibited a near identical emission spectrum with red to NIR emission (742 nm). Comparison of the emission features and WAXS and FT-IR data of the sheared n-decane film and the DMSO xerogel with the single crystal data supports a head-to-tail slipped arrangement driven by the N–H⋯F–B bonding in the sheared or xerogel states, which facilitates strong exciton coupling and the resultant NIR emission.

Graphical abstract: An unprecedented amplification of near-infrared emission in a Bodipy derived π-system by stress or gelation

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Publication details

The article was received on 17 Apr 2017, accepted on 08 Jun 2017 and first published on 08 Jun 2017


Article type: Edge Article
DOI: 10.1039/C7SC01696D
Citation: Chem. Sci., 2017,8, 5644-5649
  • Open access: Creative Commons BY license
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    An unprecedented amplification of near-infrared emission in a Bodipy derived π-system by stress or gelation

    S. Cherumukkil, S. Ghosh, V. K. Praveen and A. Ajayaghosh, Chem. Sci., 2017, 8, 5644
    DOI: 10.1039/C7SC01696D

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