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苝四甲酸二酐
	IUPAC名; Peryleno[3,4-cd:9,11-c′d′]dipyran-3,5,10,12-tetrone
别名	3,4,9,10-苝四甲酸二酐, 颜料红224
识别
CAS号	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
性质
化学式	C24H8O6
摩尔质量	392.32 g·mol⁻¹
密度	1.7 g/cm3
熔点	~350 °C
结构
晶体结构	单斜晶系, P21/c
	若非注明，所有数据均出自标准状态（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，简称PTCDA，是一种有机染料以及有机半导体分子。其为工业上制备莱啉染料的前驱体^[2]^[3]。其为深红色固体，难溶于芳香性溶剂。其常因具有半导体性质而被研究^[4]。

结构与性质

PTCDA在结构上由一个苝分子两端连接两个酸酐基团得到。其有两种晶体构型：α相和β相^[5]。且都为单斜晶系，空间群为P2₁/c。相对一般有机物，具有较高的1.7 g/cm³的密度。其晶格常数如下：

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作为有机半导体材料,拥有π电子共轭体系、可自组装形成半导体膜材料。

参考文献

^ 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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