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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
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Authors to whom correspondence should be addressed.
Academic Editor: Mitsuo Kira
Molecules 2016, 21(9), 1173; https://doi.org/10.3390/molecules21091173
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)
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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MDPI and ACS Style

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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