苝四甲酸二酐

苝四甲酸二酐
	IUPAC名; Peryleno[3,4-cd:9,11-c′d′]dipyran-3,5,10,12-tetrone
別名	3,4,9,10-苝四甲酸二酐, 顏料紅224
識別
CAS號	128-69-8
PubChem	67191
ChemSpider	60534
SMILES	c1cc2c3c(ccc4c3c1c5ccc6c7c5c4ccc7C(=O)OC6=O)C(=O)OC2=O;
InChI	1/C24H8O6/c25-21-13-5-1-9-10-2-6-15-20-16(24(28)30-23(15)27)8-4-12(18(10)20)11-3-7-14(22(26)29-21)19(13)17(9)11/h1-8H;
InChIKey	CLYVDMAATCIVBF-UHFFFAOYAS
EINECS	204-905-3
性質
化學式	C24H8O6
莫耳質量	392.32 g·mol⁻¹
密度	1.7 g/cm3
熔點	~350 °C
結構
晶體結構	單斜晶系, P21/c
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

苝四甲酸二酐（英語：Perylenetetracarboxylic dianhydride）或3,4,9,10-苝四甲酸二酐，簡稱PTCDA，是一種有機染料以及有機半導體分子。其為工業上製備萊啉染料的前驅體^[2]^[3]。其為深紅色固體，難溶於芳香性溶劑。其常因具有半導體性質而被研究^[4]。

結構與性質

PTCDA在結構上由一個苝分子兩端連接兩個酸酐基團得到。其有兩種晶體構型：α相和β相^[5]。且都為單斜晶系，空間群為P2₁/c。相對一般有機物，具有較高的1.7 g/cm³的密度。其晶格常數如下：

晶型	a	b	c	γ
α	0.374 nm	1.196 nm	1.734 nm	98.8°
β	0.378 nm	1.930 nm	1.077 nm	83.6°

PTCDA作為有機半導體材料,擁有π電子共軛體系、可自組裝形成半導體膜材料。

參考文獻

^ PTCDA.
^ Hunger, K. and Herbst, W. (2012) "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_371
^ Greene, M. (2009) "Perylene Pigments", pp. 261–274 in High Performance Pigments, Wiley-VCH, Weinheim.doi:10.1002/9783527626915.ch16
^ Russell, James C.; Blunt, Matthew O.; Goretzki, Gudrun; Phillips, Anna G.; Champness, Neil R.; Beton, Peter H. Solubilized Derivatives of Perylenetetracarboxylic Dianhydride (PTCDA) Adsorbed on Highly Oriented Pyrolytic Graphite. Langmuir. 2010, 26 (6): 3972–3974. ISSN 0743-7463. doi:10.1021/la903335v.
^ Möbus, M. & Karl, N. Structure of perylene-tetracarboxylic-dianhydride thin films on alkali halide crystal substrates. Journal of Crystal Growth. 1992, 116 (3–4): 495–504. doi:10.1016/0022-0248(92)90658-6.
^ Iwata, Kota; Yamazaki, Shiro; Mutombo, Pingo; Hapala, Prokop; Ondráček, Martin; Jelínek, Pavel; Sugimoto, Yoshiaki. Chemical structure imaging of a single molecule by atomic force microscopy at room temperature. Nature Communications. 2015, 6: 7766. PMC 4518281 . PMID 26178193. doi:10.1038/ncomms8766.
^ Cochrane, K. A.; Schiffrin, A.; Roussy, T. S.; Capsoni, M.; Burke, S. A. Pronounced polarization-induced energy level shifts at boundaries of organic semiconductor nanostructures. Nature Communications. 2015, 6: 8312. PMC 4600718 . PMID 26440933. doi:10.1038/ncomms9312.

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[1] PTCDA.

[Ullmann1-2] Hunger, K. and Herbst, W. (2012) "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_371

[3] Greene, M. (2009) "Perylene Pigments", pp. 261–274 in High Performance Pigments, Wiley-VCH, Weinheim.doi:10.1002/9783527626915.ch16

[RussellBlunt2010-4] Russell, James C.; Blunt, Matthew O.; Goretzki, Gudrun; Phillips, Anna G.; Champness, Neil R.; Beton, Peter H. Solubilized Derivatives of Perylenetetracarboxylic Dianhydride (PTCDA) Adsorbed on Highly Oriented Pyrolytic Graphite. Langmuir. 2010, 26 (6): 3972–3974. ISSN 0743-7463. doi:10.1021/la903335v.

[5] Möbus, M. & Karl, N. Structure of perylene-tetracarboxylic-dianhydride thin films on alkali halide crystal substrates. Journal of Crystal Growth. 1992, 116 (3–4): 495–504. doi:10.1016/0022-0248(92)90658-6.

[PTCDA_on_Si-6] Iwata, Kota; Yamazaki, Shiro; Mutombo, Pingo; Hapala, Prokop; Ondráček, Martin; Jelínek, Pavel; Sugimoto, Yoshiaki. Chemical structure imaging of a single molecule by atomic force microscopy at room temperature. Nature Communications. 2015, 6: 7766. PMC 4518281 . PMID 26178193. doi:10.1038/ncomms8766.

[PTCDA_on_NaCL-7] Cochrane, K. A.; Schiffrin, A.; Roussy, T. S.; Capsoni, M.; Burke, S. A. Pronounced polarization-induced energy level shifts at boundaries of organic semiconductor nanostructures. Nature Communications. 2015, 6: 8312. PMC 4600718 . PMID 26440933. doi:10.1038/ncomms9312.

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