三聚茚

三聚茚
	IUPAC名; 10,15-dihydro-5H-diindeno-[1,2-a:1',2'-c]fluorene; 10,15-二氢-5H-二茚并[1,2-a:1',2'-c]芴
识别
CAS号	548-35-6
PubChem	68355
ChemSpider	61650
SMILES	C1C2=CC=CC=C2C3=C4CC5=CC=CC=C5C4=C6CC7=CC=CC=C7C6=C31;
InChI	InChI=1S/C27H18/c1-4-10-19-16(7-1)13-22-25(19)23-14-17-8-3-6-12-21(17)27(23)24-15-18-9-2-5-11-20(18)26(22)24/h1-12H,13-15H2;
性质
化学式	C27H18
摩尔质量	342.43 g·mol−1
密度	1.286 g/cm3
熔点	378 °C（651 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

三聚茚（英语：Truxene）是一种多环芳香烃，该分子可被认为是由三个对称排列并共享一个中心苯的芴组成。三聚茚是一种固体，微溶于水。

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历史

自19世纪末以来，三聚茚就为人所知。J. Hausmann于1889年在研究3-苯基丙酸与五氧化二磷的反应时偶然发现了它。他无法确定确切的结构，但假设它是1-茚满酮的环状三聚体。据他介绍，它是由3-苯基丙酸分子内酰化产生的1-茚满酮缩合而成。^[2]

弗里德里克·基平（英语：Frederic Kipping）于1894年确定了三聚茚的结构，并通过1-茚满酮的三聚反应获得了该化合物。^[3]

制备

三聚茚通过在乙酸和浓盐酸的混合物中，由1-茚满酮的循环三聚合制备。^[4]

用途

三聚茚具有星形，因此适合作为树状物合成的起点。^[5]

三聚茚的衍生物也已用于合成液晶^[6]和富勒烯的片段。^[7]

参考资料

[1]
Harper, William L.; Smith, Wesley E. Process for synthesizing truxene; amorphous or graphitic carbon from indenes. 1970. US 3504044 A.
[2]
Hausmann, J. Einwirkung von o ‐Cyanbenzylchlorid auf Natriummalonester. Untersuchung des α‐Hydrindons. Berichte der Deutschen Chemischen Gesellschaft. July 1889, 22 (2): 2019–2026 [2022-12-12]. doi:10.1002/cber.18890220264. （原始内容存档于2022-12-12）.
[3]
Kipping, F. Stanley. XXIX. The formation of the hydrocarbon "truxene" from phenylpropionic acid, and from hydrindone. J. Chem. Soc., Trans. 1894, 65: 269–290 [2022-12-12]. doi:10.1039/CT8946500269. （原始内容存档于2022-12-12）.
[4]
Amick, Aaron Warren. Methodology Development for Use in Polycyclic Aromatic Hydrocarbon Synthesis. PhD thesis. 2008: 5.
[5]
Cao, Xiao-Yu; Zhang, Wen-Bin; Wang, Jin-Liang; Zhou, Xing-Hua; Lu, Hua; Pei, Jian. Extended π-Conjugated Dendrimers Based on Truxene. Journal of the American Chemical Society. 1 October 2003, 125 (41): 12430–12431. PMID 14531685. doi:10.1021/ja037723d.
[6]
Destrade, C.; Gasparoux, H.; Babeau, A.; Tinh, Nguyen Huu; Malthete, J. Truxene Derivatives: A New Family of Disc-Like Liquid Crystals With an Inverted Nematic-Columnar Sequence. Molecular Crystals and Liquid Crystals. May 1981, 67 (1): 37–47. doi:10.1080/00268948108070873.
[7]
Dehmlow, Eckehard V.; Kelle, Torsten. Synthesis of New Truxene Derivatives: Possible Precursors of Fullerene Partial Structures?. Synthetic Communications. June 1997, 27 (11): 2021–2031. doi:10.1080/00397919708006804.

[1] [1]
Harper, William L.; Smith, Wesley E. Process for synthesizing truxene; amorphous or graphitic carbon from indenes. 1970. US 3504044 A.

[2] [2]
Hausmann, J. Einwirkung von o ‐Cyanbenzylchlorid auf Natriummalonester. Untersuchung des α‐Hydrindons. Berichte der Deutschen Chemischen Gesellschaft. July 1889, 22 (2): 2019–2026 [2022-12-12]. doi:10.1002/cber.18890220264. （原始内容存档于2022-12-12）.

[3] [3]
Kipping, F. Stanley. XXIX. The formation of the hydrocarbon "truxene" from phenylpropionic acid, and from hydrindone. J. Chem. Soc., Trans. 1894, 65: 269–290 [2022-12-12]. doi:10.1039/CT8946500269. （原始内容存档于2022-12-12）.

[4] [4]
Amick, Aaron Warren. Methodology Development for Use in Polycyclic Aromatic Hydrocarbon Synthesis. PhD thesis. 2008: 5.

[5] [5]
Cao, Xiao-Yu; Zhang, Wen-Bin; Wang, Jin-Liang; Zhou, Xing-Hua; Lu, Hua; Pei, Jian. Extended π-Conjugated Dendrimers Based on Truxene. Journal of the American Chemical Society. 1 October 2003, 125 (41): 12430–12431. PMID 14531685. doi:10.1021/ja037723d.

[6] [6]
Destrade, C.; Gasparoux, H.; Babeau, A.; Tinh, Nguyen Huu; Malthete, J. Truxene Derivatives: A New Family of Disc-Like Liquid Crystals With an Inverted Nematic-Columnar Sequence. Molecular Crystals and Liquid Crystals. May 1981, 67 (1): 37–47. doi:10.1080/00268948108070873.

[7] [7]
Dehmlow, Eckehard V.; Kelle, Torsten. Synthesis of New Truxene Derivatives: Possible Precursors of Fullerene Partial Structures?. Synthetic Communications. June 1997, 27 (11): 2021–2031. doi:10.1080/00397919708006804.

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