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Molecules 2016, 21(9), 1173;

Effects of Substitution on Solid-State Fluorescence in 9-Aryl-9-methyl-9H-9-silafluorenes

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Authors to whom correspondence should be addressed.
Academic Editor: Mitsuo Kira
Received: 15 July 2016 / Revised: 30 August 2016 / Accepted: 31 August 2016 / Published: 3 September 2016
(This article belongs to the Special Issue Advances in Silicon Chemistry)
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Aromatic groups were incorporated into 9H-9-silafluorene units at the 9-position (mono-9H-silafluorenes) and 9,9′-positions (di-9H-9-silafluorenes). The aryl substituents showed weak conjugation to the 9H-9-silafluorene for 9-aryl substituted ones 17 and a 9,9′-phenylene substituted one (compound 8) and they exhibited similar absorption and emission spectra. The 9H-9-silafluorene 10 containing a 5,5′-(2,2′-bithiophenyl) group showed a significantly red-shifted absorption and fluorescence maxima in the solid-state. Single-crystal X-ray diffraction studies found J-type aggregated structures formed by intermolecular CH–π interactions (ca. 2.6–2.7 Å). Density functional theory (DFT), time-dependent DFT (TD-DFT), and configuration interaction single (CIS) calculations were conducted to explain the observed optical properties. View Full-Text
Keywords: 9H-9-silafluorene; thiophene; UV absorption; solid-state emission; single-crystal X-ray diffraction; J-aggregation 9H-9-silafluorene; thiophene; UV absorption; solid-state emission; single-crystal X-ray diffraction; J-aggregation

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Yamanoi, Y.; Nakashima, T.; Shimada, M.; Maeda, H.; Nishihara, H. Effects of Substitution on Solid-State Fluorescence in 9-Aryl-9-methyl-9H-9-silafluorenes. Molecules 2016, 21, 1173.

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