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

Kitamura, Chitoshi; Abe, Yasushi; Ohara, Takuya; Yoneda, Akio; Kawase, Takeshi; Kobayashi, Takashi; Naito, Hiroyoshi; Komatsu, Tatsuya

doi:10.1002/chem.200901668

Cited by 73 publications

(46 citation statements)

References 44 publications

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“…In this paper, one will focus on the six most representative families of compounds displaying color polymorphism, whose most famous members are represented in Fig. 2: N-(4-methyl-2-nitrophenyl) acetamide [20][21][22][23][24][25][26] , dimethyl 2,5-dichloro-3,6-dihydroxyterephthalate [27][28][29][30][31][32][33][34][35] , 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrile (ROY) [36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51][52][53] , 2,4,6-trinitro-N-(p-tolyl)aniline [54][55][56][57][58][59][60][61] , dimethyl-5-benzoyl-3-phenylindolizine-1,2-dicarboxylate 14 , and 1,4,7,10-tetrabutyltetracene [62][63][64] .…”

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confidence: 99%

Color polymorphism in organic crystals

2020

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Color polymorphism is an interesting property of chemical systems which present crystal polymorphs of different colors. It is a rare phenomenon, with only a few examples reported in the literature hitherto. Nevertheless, systems exhibiting color polymorphism have many potential applications in different domains, such as pigment, sensor, and technology industries. Here, known representative chemical systems showing color polymorphism are reviewed, and the reasons for them to present such property discussed. Also, since some of the concepts related to color polymorphism have been frequently used imprecisely in the scientific literature, this article provides concise, systematic definitions for these concepts. T his paper focuses on color polymorphism, a fascinating property exhibited by chemical systems that present polymorphs showing different colors. In the first few sections, unambiguous definitions of the structural properties and of the relevant physical concepts related with this subject will be provided, since some of them have been frequently used in an imprecise way in the scientific literature. Then, the physicochemical reasons leading to color polymorphism will be described briefly using an essentially phenomenological approach. The last few sections of this paper will survey representative chemical systems showing color polymorphism. Terminology Polymorphism. In the crystallographic context, polymorphism, from the Greek poly (many) and morphe (form), also known as crystal polymorphism, refers to the ability of a certain compound to exist in different crystallographic structures, resulting from different packing arrangements of its molecules in the crystal structure 1. It is worth to differentiate between polymorphism and allotrophism. While the latter term describes the existence of different crystal structures of the same element, polymorphism is used regarding different crystalline structures of compounds. It is also important to mention that in this review, one will not consider solvates, hydrates, or dynamic isomers (including geometric isomers and tautomers) as polymorphic phases, but instead, as pseudopolymorphic states. Hence, a safe criterion for the classification of a system as polymorphic would be if the crystal structures are different but give rise to the same liquid and vapor states. Why is polymorphism so important? The main reason is that although being composed of the same compound, different polymorphic structures can behave as different materials 2. Indeed, in

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confidence: 99%

Color polymorphism in organic crystals

2020

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“…DFT calculations on the B3LYP/6‐31G** level, as similarly applied by others in related studies,20e, 35a revealed that the tristetracenes 9 and 10 have their highest occupied molecular orbitals (HOMOs; A 2 symmetry) and lowest occupied molecular orbitals (LUMOs; A 1 ) spread about the whole C 3 v ‐symmetrical molecular framework (see the Supporting Information) 36. Compared with 9 , the energies of the occupied MOs of 10 are slightly increased, whereas the increase of the LUMO energies is negligible.…”

Section: Resultsmentioning

confidence: 73%

Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes

Mughal

Eberhard

Kuck

2013

Chemistry A European J

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The linear extension of the rigid, C(3v)-symmetrical carbon framework of tribenzotriquinacene (TBTQ) along its three wings is reported. The key step of the extension procedure consists of a Diels-Alder reaction of three ortho-quinodimethane units generated in situ at the triquinacene core. The use of 1,4-naphthoquinone provides a facile and particularly efficient access to tris(tetraceno)-annellated triquinacenes. The steady-state photophysical properties of these new oligotetracenes bearing three mutually orthogonal chomophores are determined and analyzed by DFT calculations.

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“…Kitamura et al. reported that, in the solid state, the UV/Vis spectra of 1,4,7,10‐tetraalkyltetracenes strongly depended on the length of the alkyl substituents . Similarly, UV/Vis and fluorescence spectral changes by varying the alkyl chain lengths have been reported for a number of π‐conjugated systems .…”

Section: Introductionmentioning

confidence: 94%

“…[7][8][9] Kitamura et al reported that, in the solid state, the UV/Vis spectrao f 1,4,7,10-tetraalkyltetracenes strongly dependedo nt he length of the alkyl substituents. [10] Similarly,U V/Vis and fluorescence spectralc hanges by varying the alkyl chain lengths have been reportedf or an umber of p-conjugated systems. [11] Konishi et al prepared pyrene derivatives with mono-to tetraalkyl substituents and investigated their photophysical properties, demonstrating the alkyl substituent effects on the pyrene chromophores,b ut the solid-state photophysical properties were not examined.…”

Section: Introductionmentioning

confidence: 99%

Molecular Packing and Solid‐State Photophysical Properties of 1,3,6,8‐Tetraalkylpyrenes

Iwasaki

Murakami

Takeda

et al. 2019

Chemistry A European J

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The relationship between the photophysical properties and molecular orientation of 1,3,6,8‐tetraalkylpyrenes in the solid state is described herein. The introduction of alkyl groups with different chain structures (in terms of length and branching) did not affect the photophysical properties in solution, but significantly shifted the emission wavelengths and fluorescence quantum yields in the solid state for some samples. Pyrenes bearing ethyl, isobutyl, or neopentyl groups at the 1‐, 3‐, 6‐, and 8‐positions showed similar emission profiles in both the solution and solid states. In contrast, pyrenes bearing other alkyl groups exhibited an excimer emission in the solid state, similar to that of the parent pyrene. On studying the photophysical properties in the solid state with respect to the obtained crystal structures, the observed solid‐state photophysical properties were found to depend on the relative position of the pyrene chromophores. The solid‐state photophysical properties can be controlled by the alkyl groups, which provide changing crystal packing. Among the pyrenes tested, 1,3,6,8‐tetraethylpyrene showed the highest fluorescence quantum yield of 0.88 in the solid state.

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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

Cited by 73 publications

References 44 publications

Color polymorphism in organic crystals

Color polymorphism in organic crystals

Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes

Molecular Packing and Solid‐State Photophysical Properties of 1,3,6,8‐Tetraalkylpyrenes

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