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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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Supplementary files

Article information


Submitted
31 Jan 2017
Accepted
27 May 2017
First published
29 May 2017

New J. Chem., 2017,41, 6025-6032
Article type
Paper

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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