Conformational polymorphism and optical properties in the solid state of 1,4,7,10-tetra(n-butyl)tetracene

Kitamura, Chitoshi; Ohara, Takuya; Kawatsuki, Nobuhiro; Yoneda, Akio; Kobayashi, Takashi; Naito, Hiroyoshi; Komatsu, Tatsuya; Kitamura, Teruo

doi:10.1039/b707685c

Cited by 59 publications

(27 citation statements)

References 13 publications

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“…[6] The images in Figure 1 show this solid-state crystallochromic effect for the alkylsubstituted tetracene series-to our knowledge, the first case of crystallochromy among acenes. The colors range from yellow (ethyl (1 b) and butyl (1 d-form B) derivatives) to orange (methyl (1 a), propyl (1 c), and pentyl (1 e) deriva- Optical properties of 1,4,7,10-tetraalkyltetracenes in solution and in the solid state: UV/Vis absorption and fluorescence spectra for 1 a-f, both in hexane and in the solid state, are shown in Figure 2.…”

Section: Resultsmentioning

confidence: 92%

“…As we already reported, 1 d-form A and 1 dform B are conformational polymorphs of the same molecule. [6] Interestingly, solids with similar molecular structures have similar colors: 1 b and 1 d-form B are yellow; 1 c and 1 e are orange; and 1 d-form A and 1 f are red. All of the alkyl side chains take an all-trans planar conformation.…”

Section: Resultsmentioning

confidence: 93%

“…A recently published preliminary report indicated that 1 d exists as two conformational polymorphic forms composed of yellow and red solids. [6] In this paper, we describe the synthesis of a series of alkyl-substituted tetracenes 1 a-f, optical properties of the tetracenes in the solid state, and X-ray crystallographic analyses. We also discuss a possible mechanism for solidstate color change governed by the alkyl side-chain length.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Crystallochromy of 1,4,7,10‐Tetraalkyltetracenes: Tuning of Solid‐State Optical Properties of Tetracenes by Alkyl Side‐Chain Length

Kitamura

Abe

Ohara

et al. 2010

Chemistry A European J

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We synthesized a series of 1,4,7,10-tetraalkyltetracenes using a new 2,6-naphthodiyne precursor and 2,5-dialkylfurans as starting materials (alkyl=methyl to hexyl). Surprisingly, the solid-state color of the tetracenes ranges through yellow, orange, and red. Both yellow and red solids are obtained for the butyl derivative. Optical properties in solution show no marked differences; however, those in the solid state show characteristics that vary with alkyl side-chain length: methyl, propyl, and pentyl derivatives are orange; ethyl and butyl derivatives are yellow; and another butyl and hexyl derivative are red. X-ray analyses reveal that the molecular structures are planar, semi-chair, or chair forms; the chair form takes a herringbone-like arrangement and the other forms take slipped parallel arrangements. The mechanism of crystallochromy is discussed in terms of molecular structure, crystal packing, and calculations that take account of exciton coupling.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Crystallochromy of 1,4,7,10‐Tetraalkyltetracenes: Tuning of Solid‐State Optical Properties of Tetracenes by Alkyl Side‐Chain Length

Kitamura

Abe

Ohara

et al. 2010

Chemistry A European J

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“…[3] 2,5-Diisobutylfuran (4b) and 2,5-diisopentylfuran (4c) were easily prepared by nucleophilic substitution reaction of 2,5-dilithiated furan with the corresponding alkyl halides. However, 2,5-diisopropylfuran (4a) could not be obtained by this method.…”

Section: Synthesis Of 14710-tetraisoalkyltetracenesmentioning

confidence: 99%

“…Therefore many groups have increasingly performed acene functionalizations and reported various substituted oligoacenes. [2] We recently prepared a series of linear alkyl-substituted tetracenes [3] (1a-f; Scheme 1). We then elucidated the effects of their linear alkyl side-chains on packing patterns and solid-state optical properties.…”

Section: Introductionmentioning

confidence: 99%

1,4,7,10‐Tetraisoalkyltetracenes: Tuning of Solid‐State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

et al. 2010

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We have synthesized 1,4,7,10-tetraisoalkyltetracenes from a 2,6-naphthodiyne precursor and 2,5-diisoalkylfurans as the starting materials (isoalkyl: isopropyl, isobutyl, and isopentyl). The tetracene molecules exhibited crystallochromy: The solid-state colors of the isopropyl, isobutyl, and isopentyl derivatives were yellow, red, and orange-yellow, respectively. In contrast, there were no marked differences in the optical properties of these compounds in solution. The isopropyl derivative exhibited the highest fluorescence quantum yield in

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Synthesis of Substituted Oligoacenes via Diels–Alder Reactions and Substituent Effects on Molecular Structure, Packing Arrangement, and Solid‐State Optical Properties

Kitamura

2014

Methods and Applications of Cycloaddition Reactions in Organic Syntheses

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Conformational polymorphism and optical properties in the solid state of 1,4,7,10-tetra(n-butyl)tetracene

Cited by 59 publications

References 13 publications

Synthesis and Crystallochromy of 1,4,7,10‐Tetraalkyltetracenes: Tuning of Solid‐State Optical Properties of Tetracenes by Alkyl Side‐Chain Length

Synthesis and Crystallochromy of 1,4,7,10‐Tetraalkyltetracenes: Tuning of Solid‐State Optical Properties of Tetracenes by Alkyl Side‐Chain Length

1,4,7,10‐Tetraisoalkyltetracenes: Tuning of Solid‐State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

Synthesis of Substituted Oligoacenes via Diels–Alder Reactions and Substituent Effects on Molecular Structure, Packing Arrangement, and Solid‐State Optical Properties

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