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Issue 33, 2019
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Syntheses and quadratic nonlinear optical properties of 2,7-fluorenylene- and 1,4-phenylene-functionalized o-carboranes

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Abstract

o-Carboranes C-functionalized by (4-substituted-phen-1-yl)ethynyl-1,4-phenyl groups or (2-substituted-fluoren-7-yl)ethynyl-2,7-fluorenyl groups, in which the pendant functionalization is electron-withdrawing nitro or electron-donating diphenylamino groups, have been synthesized and in many cases structurally characterized. Diphenylamino-containing examples coupled via the two π-delocalizable bridges to the electron-accepting o-carborane unit exhibit the greater quadratic optical nonlinearities at 1064 nm (hyper-Rayleigh scattering, ns pulses), the nonlinearities also increasing on proceeding from 1,4-phenylene- to 2,7-fluorenylene-containing bridge. The most NLO-efficient example 2-(n-butyl)-1-(2-((9,9-di(n-butyl)-2-(N,N-diphenylamino)-9H-fluoren-7-yl)ethynyl)-9,9-di(n-butyl)-9H-fluoren-7-yl)-1,2-ortho-carborane, consisting of diphenylamino donor, fluorenyl-containing bridge, o-carborane acceptor, and solubilizing n-butyl units, exhibits large 〈βHRS (230 × 10−30 esu) and frequency-independent (two-level model) 〈β0〉 (96 × 10−30 esu) values. Coupling two (2-((9,9-di(n-butyl)-2-(N,N-diphenylamino)-9H-fluoren-7-yl)ethynyl)-9,9-di(n-butyl)-9H-fluoren-7-yl) units to the 1,2-ortho-carborane core affords a di-C-functionalized compound with enhanced nonlinearities (309 × 10−30 esu and 129 × 10−30 esu, respectively).

Graphical abstract: Syntheses and quadratic nonlinear optical properties of 2,7-fluorenylene- and 1,4-phenylene-functionalized o-carboranes

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Publication details

The article was received on 24 Jun 2019, accepted on 26 Jul 2019 and first published on 29 Jul 2019


Article type: Paper
DOI: 10.1039/C9DT02645B
Dalton Trans., 2019,48, 12549-12559

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    Syntheses and quadratic nonlinear optical properties of 2,7-fluorenylene- and 1,4-phenylene-functionalized o-carboranes

    P. Jiang, Z. Wang, G. J. Moxey, M. Morshedi, A. Barlow, G. Wang, C. Quintana, C. Zhang, M. P. Cifuentes and M. G. Humphrey, Dalton Trans., 2019, 48, 12549
    DOI: 10.1039/C9DT02645B

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