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Issue 13, 2017
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Laterally stretched polycyclic aromatic hydrocarbons: synthesis of dibenzophenanthroheptaphene and tetrabenzotriphenylenopyranthrene derivatives

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Abstract

Efficient methods for the synthesis of dibenzophenanthroheptaphene (DBPH) and tetrabenzotriphenylenopyranthrene (TBTP) were developed. As a result, a series of unprecedented derivatives of DBPH (1a–c) and TBTP (2a–b) were conventionally obtained from the Scholl cyclodehydrogenation reaction of their respective tribenzopentaphene synthons. An alternative convergent synthesis of DBPH is also shown herein. The novel compounds were fully characterized by high-resolution matrix-assisted laser desorption ionization time of flight mass spectrometry (HR-MALDI-TOF-MS), nuclear magnetic resonance (NMR), UV-Vis absorption and emission spectroscopy. In addition, density functional calculations were carried out to gain insight into the structure and electronic properties of these novel molecules, which corroborates the experimental observations.

Graphical abstract: Laterally stretched polycyclic aromatic hydrocarbons: synthesis of dibenzophenanthroheptaphene and tetrabenzotriphenylenopyranthrene derivatives

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Publication details

The article was received on 31 Jan 2017, accepted on 27 May 2017 and first published on 29 May 2017


Article type: Paper
DOI: 10.1039/C7NJ00371D
Citation: New J. Chem., 2017,41, 6025-6032
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    Laterally stretched polycyclic aromatic hydrocarbons: synthesis of dibenzophenanthroheptaphene and tetrabenzotriphenylenopyranthrene derivatives

    B. Alameddine, R. S. Anju, S. Shetty, N. Baig, F. Al-Sagheer, S. Al-Mousawi and T. A. Jenny, New J. Chem., 2017, 41, 6025
    DOI: 10.1039/C7NJ00371D

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