Laterally stretched polycyclic aromatic hydrocarbons: synthesis of dibenzophenanthroheptaphene and tetrabenzotriphenylenopyranthrene derivatives. (12th June 2017)

• Record Type: Journal Article
• Authors: Alameddine, Bassam; Anju, Rajamohanan Sobhana; Shetty, Suchetha; Baig, Noorullah; Al-Sagheer, Fakhreia; Al-Mousawi, Saleh; Jenny, Titus Andreas
• Is Part Of: New journal of chemistry. Volume 41:Number 13(2017)
• Page Start: 6025
• Page End: 6032
• Publication Date: 2017-06-12
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c7nj00371d
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : The synthesis of new extended trapezoidal PAHs is shown. Tetra-alkylation of the most stretched derivative induces a contorted structure. 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.