Hydrosolubilization of large aromatic molecules: Facile synthesis and characterization of water-soluble derivatives of decacyclene

Aldo Arrais; Eliano Diana

doi:10.1081/SCC-120023991

Hydrosolubilization of large aromatic molecules: Facile synthesis and characterization of water-soluble derivatives of decacyclene

Aldo Arrais
, Eliano Diana

Research output: Contribution to journal › Article › peer-review

Abstract

Application of a mild-condition reductive/oxidative protocol to the large poorly-conjugated aromatic structure of decacyclene affords a water soluble oxygenated amphiphilic material which has been characterized and compared with the hydrocarbon precursor by means of solution ¹H NMR and solid-state ¹³C CPMAS NMR, vibrational, electron, and mass spectroscopies. The nature of the different oxygenated moieties covalently attached to decacyclene framework is elucidated and the role of molecular O ₂ in the oxidizing reaction path of reduced decacyclene is discussed.

Original language	English
Pages (from-to)	3331-3345
Number of pages	15
Journal	Synthetic Communications
Volume	33
Issue number	19
DOIs	https://doi.org/10.1081/SCC-120023991
Publication status	Published - 2003
Externally published	Yes

Keywords

Polyaromatic hydrocarbons
Solid state spectroscopy
Water solubility

Access to Document

10.1081/SCC-120023991

Cite this

@article{9b80942d3d5d40149768c08a42d8a844,

title = "Hydrosolubilization of large aromatic molecules: Facile synthesis and characterization of water-soluble derivatives of decacyclene",

abstract = "Application of a mild-condition reductive/oxidative protocol to the large poorly-conjugated aromatic structure of decacyclene affords a water soluble oxygenated amphiphilic material which has been characterized and compared with the hydrocarbon precursor by means of solution 1H NMR and solid-state 13C CPMAS NMR, vibrational, electron, and mass spectroscopies. The nature of the different oxygenated moieties covalently attached to decacyclene framework is elucidated and the role of molecular O 2 in the oxidizing reaction path of reduced decacyclene is discussed.",

keywords = "Polyaromatic hydrocarbons, Solid state spectroscopy, Water solubility",

author = "Aldo Arrais and Eliano Diana",

note = "Funding Information: Authors are kindly indebted to Prof. Roberto Gobetto (Dipartimento di Chimica I.F.M., University of Turin, Italy), for a helpful discussion on acquired NMR spectra, and to Dr. Angelo Agostino (Dipartimento di Chimica Generale e Organica Applicata, University of Turin, Italy), for the performing of EDX analysis. Fund grant from the Ministero dell{\textquoteright}Istruzione, Universit{\`a} e Ricerca (MIUR) is gratefully acknowledged.",

year = "2003",

doi = "10.1081/SCC-120023991",

language = "English",

volume = "33",

pages = "3331--3345",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "19",

}

TY - JOUR

T1 - Hydrosolubilization of large aromatic molecules

T2 - Facile synthesis and characterization of water-soluble derivatives of decacyclene

AU - Arrais, Aldo

AU - Diana, Eliano

N1 - Funding Information: Authors are kindly indebted to Prof. Roberto Gobetto (Dipartimento di Chimica I.F.M., University of Turin, Italy), for a helpful discussion on acquired NMR spectra, and to Dr. Angelo Agostino (Dipartimento di Chimica Generale e Organica Applicata, University of Turin, Italy), for the performing of EDX analysis. Fund grant from the Ministero dell’Istruzione, Università e Ricerca (MIUR) is gratefully acknowledged.

PY - 2003

Y1 - 2003

N2 - Application of a mild-condition reductive/oxidative protocol to the large poorly-conjugated aromatic structure of decacyclene affords a water soluble oxygenated amphiphilic material which has been characterized and compared with the hydrocarbon precursor by means of solution 1H NMR and solid-state 13C CPMAS NMR, vibrational, electron, and mass spectroscopies. The nature of the different oxygenated moieties covalently attached to decacyclene framework is elucidated and the role of molecular O 2 in the oxidizing reaction path of reduced decacyclene is discussed.

AB - Application of a mild-condition reductive/oxidative protocol to the large poorly-conjugated aromatic structure of decacyclene affords a water soluble oxygenated amphiphilic material which has been characterized and compared with the hydrocarbon precursor by means of solution 1H NMR and solid-state 13C CPMAS NMR, vibrational, electron, and mass spectroscopies. The nature of the different oxygenated moieties covalently attached to decacyclene framework is elucidated and the role of molecular O 2 in the oxidizing reaction path of reduced decacyclene is discussed.

KW - Polyaromatic hydrocarbons

KW - Solid state spectroscopy

KW - Water solubility

UR - https://www.scopus.com/pages/publications/0041331457

U2 - 10.1081/SCC-120023991

DO - 10.1081/SCC-120023991

M3 - Article

SN - 0039-7911

VL - 33

SP - 3331

EP - 3345

JO - Synthetic Communications

JF - Synthetic Communications

IS - 19

ER -

Hydrosolubilization of large aromatic molecules: Facile synthesis and characterization of water-soluble derivatives of decacyclene

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this