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8-[2-(1H-indol-3-yl)vinyl]-10,10-dimethyl-10H-pyrido[1,2-a] indolium Perchlorate

College of Chemistry and Material Science, Shandong Agricultural University, Tai’an, 271018, China
Department of Chemistry and Chemical Engineering, Heze University, Heze, 274015, China
Author to whom correspondence should be addressed.
Molbank 2010, 2010(4), M699;
Submission received: 10 August 2010 / Accepted: 13 October 2010 / Published: 14 October 2010


A novel compound, 8-[2-(1H-indol-3-yl)vinyl)]-10,10-dimethyl-10H-pyrido[1,2-a]indolium perchlorate, was synthesized by the condensation of 8,10,10-trimethyl-10H- pyrido[1,2-a]indolium perchlorate and indole-3-carbaldehyde in the presence of piperidine. The structure of the target compound was characterized by IR, 1H NMR and elemental analysis, and its UV-visible absorption and emission spectra were also determined.

Graphical Abstract

The substituted 10H-pyrido[1,2-a]indolium perchlorates can be used as photosensitive dyes, fluorescent whiteners and organic light-guide sensitizers [1,2]. Many of this kind of compounds have been synthesized, such as methyl, phenyl, styryl or furyl-substituted 10H-pyrido[1,2-a]indolium perchlorates [3,4,5,6]. In order to study the relationship between the structure and absorption maximum (λmax), the crystal structures of some compounds in this series were determined [7,8], and found that the introduction of a conjugation group in the 8-position significantly increases the λmax. To obtain a compound with a larger λmax, herein, we introduced 2-(1H-indol-3-ly)vinyl (a group making up a conjugated system with the 10H-pyrido[1,2-a]indole moiety) onto 8-position and synthesized the target compound.
Molbank 2010 m699 i001


A mixture of 8,10,10-trimethyl-10H-pyrido[1,2-a]indolium perchlorate (0.62 g, 0.002 mol), indole-3-carbaldehyde (0.29 g, 0.002 mol) and piperidine (6 drops) in ethanol (15 mL) was refluxed for 3 h with stirring to give a brown precipitate. The solid was filtered off and recrystallized from methanol/ acetonitrile to yield the target compound as orange crystals.
Yield: 70%; Melting point: 271–273 °C.
IR (KBr) v cm–1: 3310 (N-H), 1600 (C=N+), 1365{C(CH3)2}, (1090, 623 (ClO4¯), 965 {H-C=C-H (E)}.
UV-Vis (EtOH): λmax = 480.5 nm; ε = 4.68 ×104 cm2•mol -1.
1H NMR (400 MHz, DMSO-d6) δ ppm: 11.99 (s, 1H, N-H), 9.52 (d, 1H, J = 6.8 Hz, 6-H), 8.59 (s, 1H, 9-H), 8.39 (d, 1H, J = 16.1 Hz, 12-H), 8.29 (d, 1H, J = 7.4 Hz, 7-H), 8.00 (s, 1H, pyrrole-C-H), 7.42 (d, 1H, J = 16.1 Hz, 11-H), 7.27-8.22 (m, 8H, Ph-H), 1.72 (s, 6H, 2×CH3).
Elemental analysis: Calcd for C24H21ClN2O4 C, 65.98%, H, 4.84%, N, 6.41%. Found: C, 65.75%, H, 4.93%, N, 6.75%.
Figure 1. UV-Visible absorption (left) and emission spectrum (right) of the target compound.
Figure 1. UV-Visible absorption (left) and emission spectrum (right) of the target compound.
Molbank 2010 m699 g001

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References and Notes

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Share and Cite

MDPI and ACS Style

Cao, P.; Jiang; Zhang, X.-B.; Ge, S.-Z. 8-[2-(1H-indol-3-yl)vinyl]-10,10-dimethyl-10H-pyrido[1,2-a] indolium Perchlorate. Molbank 2010, 2010, M699.

AMA Style

Cao P, Jiang, Zhang X-B, Ge S-Z. 8-[2-(1H-indol-3-yl)vinyl]-10,10-dimethyl-10H-pyrido[1,2-a] indolium Perchlorate. Molbank. 2010; 2010(4):M699.

Chicago/Turabian Style

Cao, Peng, Jiang, Xue-Bin Zhang, and Shang-Zheng Ge. 2010. "8-[2-(1H-indol-3-yl)vinyl]-10,10-dimethyl-10H-pyrido[1,2-a] indolium Perchlorate" Molbank 2010, no. 4: M699.

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