Pyrene

3 Key excerpts on "Pyrene"

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  eBook - PDF

  Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 45b

  Aromatic Ring Assemblies, Polycyclic Aromatic Hydrocarbons, and Conjugated Polyenes

  • Jay Siegel, Yoshito Tobe, Jay Siegel, Yoshito Tobe(Authors)
  • 2014(Publication Date)
  • Thieme Chemistry

    (Publisher)

  45.22.1 Product Subclass 1: Pyrenes, Cyclopenta[cd]Pyrenes, and BenzoPyrenes Pyrene and some of its derivatives, especially cyclopenta[cd]Pyrene and benzo[a]Pyrene, are environmental pollutants. [4] They are produced by incomplete combustion of some or- ganic substances, such as gasoline, kerosene, and coal. [5,6] Section 45.22.1.1.1 covers the synthesis of the parent Pyrene and various substituted derivatives whilst cyclopenta[cd]Pyrenes are described in Section 45.22.1.1.2. Sections for references see p 1012 956 Science of Synthesis 45.22 Pyrenes, Circulenes, and Other Condensed Acenes 45.22.1.1.3 and 45.22.1.1.4 cover benzoPyrenes, Sections 45.22.1.1.5–45.22.1.1.8 describe dibenzoPyrenes, and Sections 45.22.1.1.9 and 45.22.1.1.10 discuss naphthoPyrenes. According to CAS nomenclature, which is used for the ring systems in this section, the dibenzoPyrenes are named as dibenzo[b,def]chrysene (dibenzo[a,h]Pyrene), ben- zo[rst]pentaphene (dibenzo[a,i]Pyrene), dibenzo[def,p]chrysene (dibenzo[a,l]Pyrene), and dibenzo[fg,op]naphthacene (dibenzo[e,l]Pyrene), and the naphthoPyrenes are named as di- benzo[c,mno]chrysene and naphtho[8,1,2-ghi]chrysene. 45.22.1.1 Synthesis of Product Subclass 1 45.22.1.1.1 Pyrenes 45.22.1.1.1.1 Method 1: Synthesis from [2.2]Metacyclophanes 45.22.1.1.1.1.1 Variation 1: Cycloaromatization In the presence of palladium on charcoal at high temperatures (~300 8C), the [2.2]metacy- clophanes 6 (R 1 = H, Me) undergo cycloaromatization to form the corresponding Pyrenes 7 (Scheme 2). [7,8] 2,7-DimethylPyrene (7, R 1 = Me) can be prepared from the corresponding cyclophane 6 (R 1 = Me) by radical cyclization in the presence of dibenzoyl peroxide, fol- lowed by transannular dehydrogenation and aromatization; the disadvantage of this sim- ple reaction is its low yield.

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  eBook - ePub

  Organic Nanoreactors

  From Molecular to Supramolecular Organic Compounds

  • Samahe Sadjadi(Author)
  • 2016(Publication Date)
  • Academic Press

    (Publisher)

  10. New York : Springer Science + Business Media ; 2005 : 211. [15] Becker RS, Singh IS, Jackson EA. Comprehensive spectroscopic investigation of polynuclear aromatic hydrocarbons. I. absorption spectra and state assignments for the tetracyclic hydrocarbons and their alkyl-substituted derivatives. J Chem Phys. 1963 ; 38 : 2144 – 2171. [16] Tanaka J. The electronic spectra of Pyrene, chrysene, azulene, coronene and tetracene crystals. Bull Chem Soc Jpn. 1965 ; 38 : 86 – 102. [17] Mangle EA, Topp MR. Excited-state dynamics of jet-cooled Pyrene and some molecular complexes. J Phys Chem. 1986 ; 90 : 802 – 807. [18] Kerkines ISK, Petsalakis ID, Theodorakopoulos G, Klopper W. Low-lying absorption and emission spectra of Pyrene, 1,6-dithiaPyrene, and tetrathiafulvalene: A comparison between ab initio. and time-dependent density functional methods. J Chem Phys. 2009 ; 131 : 224315. [19] Bito Y, Shida N, Toru T. Ab initio MRSD-CI calculations of the ground and the two lowest-lying excited states of Pyrene. Chem Phys Lett. 2000 ; 328 : 310 – 315. [20] Okamoto A, Kanatani K, Saito I. Pyrene-labeled base-discriminating fluorescent DNA probes for homogeneous SNP typing. J Am Chem Soc. 2004 ; 126 : 4820 – 4827. [21] Langenegger SM, Haner R. Excimer formation by interstrand stacked Pyrenes. Chem. Commun. 2004 : 2792 – 2793. [22] Otsubo T, Aso Y, Takimiya K. Functional oligothiophenes as advanced molecular electronic materials. J Mater Chem. 2002 ; 12 : 2565 – 2575. [23] Jia W-L, Cormick TMc, Liu Q-D, Fukutani H, Motala M, Wang R-Y, Tao Y, Wang S. Diarylamino functionalized Pyrene derivatives for use in blue OLEDs and complex formation. J Mater

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  Theoretical and Computational Chemistry Aspects

  • Ponnadurai Ramasami(Author)
  • 2021(Publication Date)
  • De Gruyter

    (Publisher)

  Besides, their excellent fl uo-rescent properties have been attributed to their extended delocalized π -electrons [5]. Besides, these electrons are also responsible for different kinds of π -interactions via their unique bonding modes [6 – 9]. However, their low solubility and nonexistence of suitable methods for chemical transformations have constrained their widespread use as materials. Nevertheless, PACs with four membered (fused) rings have attracted the scienti fi c community because of their unique nature [10 – 13] and suitably explored as energy related applications and in organic electronics [14 – 16]. Pyrene can be considered as the molecular fragments of carbon nano allotropes viz. graphene and carbon nanotubes [17, 18]. Owing to the conjugated macrocyclic *Corresponding author: Bapan Saha , Department of Chemistry, Handique Girls ’ College, Guwahati, 781001, Assam, India, E-mail: [email protected] Pradip Kumar Bhattacharyya, Arya Vidyapeeth College, Guwahati, 781016, Assam, India, E-mail: [email protected] This article has previously been published in the journal Physical Sciences Reviews. Please cite as: B. Saha and P. K. Bhattacharyya “ Role of heteroatoms and substituents on the structure, reactivity, aromaticity, and absorption spectra of Pyrene: a density functional theory study ” Physical Sciences Reviews [Online] 2021, 7. DOI: 10.1515/psr-2020-0086 | https://doi.org/10.1515/9783110739763-001 π -delocalized structure, Pyrene-based materials have been explored in developing light emitting (organic electronics) and charge transport materials [11, 14]. Recently, Pyrene-based molecules are being extensively used for functionalization of carbon nanotubes and in anchoring of foreign molecules such as polymers, proteins, small biomolecules and many more [19 – 21]. Besides, their use in studying protein and nucleic acids, such materials has also been explored in sensing oxygen, intercalating DNA, and solar cells [22 – 24].

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