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Volume 2010
Issue 4
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Short Note

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

by
Peng Cao
1,
Jiang
1,*,
Xue-Bin Zhang
1 and
Shang-Zheng Ge
2
1
College of Chemistry and Material Science, Shandong Agricultural University, Tai’an, 271018, China
2
Department of Chemistry and Chemical Engineering, Heze University, Heze, 274015, China
*
Author to whom correspondence should be addressed.
Molbank 2010, 2010(4), M699; https://doi.org/10.3390/M699
Submission received: 10 August 2010 / Accepted: 13 October 2010 / Published: 14 October 2010
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Abstract

:
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

Experimental

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%.
Molbank 2010 m699 g001 550
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

  1. McColgin, W.C.; Chapman, D.D. Dye laser and method. U.S. Patent 3,860,866, 14 January 1975. [Google Scholar]
  2. Liu, Z.J.; Nan, Z.X.; Zhang, Z.J.; Huang, Y.Q. Synthesis of 8-(4-substituted phenyl)-10,10-dimethyl-6-phenyl-10H-pyrido[1,2-a]indolium perchlorate. Chin. J. Org. Chem. 1984, 4, 369–370. [Google Scholar]
  3. Chapman, D.D.; Elwood, J.K.; Heseltine, D.W.; Hess, H.M.; Kurtz, D.W. Annelation of pyridinium rings onto nitrogen heterocycles. J. Org. Chem. 1977, 42, 2474–2480. [Google Scholar] [CrossRef]
  4. Liu, Z.J.; Gong, Y.; Chen, S.H.; Cao, J.J. Synthesis of 6-(4-substitutedstyryl)-8-(4-substituted phenyl)-10,10-dimethyl-10H-pyrido[1,2-a]indolium perchlorate. Chin. J. Org. Chem. 1987, 7, 137–139. [Google Scholar]
  5. Liu, Z.J.; Li, W.G.; Zhang, J.H.; Gong, Y. Syntheses and 1H NMR studies of substituted styryl-10H-pyrido[1,2-a]indolium perchlorates. Chem. J. Chin. Univ. 1992, 13, 470–473. [Google Scholar]
  6. Li, Z.J.; Zhou, J.W. Synthesis and spectral properties of 10,10-dimethyl-6-phenyl-8-(5-substituted-2-furyl)-10H-pyrido[1,2-a]indolium salts. Chin. Sci. Bull. 1987, 32, 188–190. [Google Scholar]
  7. Jiang, L.; Wang, J.M.; Li, C.C. Synthesis and Crystal Structure of 6-(3-indolyl)-8-(p-chlorophenyl)-10,10-dimethyl-10H-pyrido[1,2-a]indolium perchlorate. Chin. J. Struct. Chem. 2004, 23, 1371–1375. [Google Scholar]
  8. Chen, S.H.; Xu, X.W.; Wang, N.N. Preparation and crystal structure of 9,9-dimethyl-2-(4-methoxyphenyl)-4-phenyl-9H-pyrido[1,2-a]indolium perchlorate under microwave radiation. Chin. J. Org. Chem. 2008, 28, 353–355. [Google Scholar] [CrossRef]

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. https://doi.org/10.3390/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. https://doi.org/10.3390/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. https://doi.org/10.3390/M699

APA Style

Cao, P., Jiang, Zhang, X. -B., & Ge, S. -Z. (2010). 8-[2-(1H-indol-3-yl)vinyl]-10,10-dimethyl-10H-pyrido[1,2-a] indolium Perchlorate. Molbank, 2010(4), M699. https://doi.org/10.3390/M699

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