An orthogonal C-H borylation--cross-coupling strategy for the preparation of tetrasubstituted "A2B2"-chrysene derivatives with tuneable photophysical properties.

نویسندگان

  • K W J Heard
  • J J Morrison
  • L Weston
  • C H Lo
  • L Pirvu
  • J Raftery
  • M S Little
  • J J W McDouall
  • S G Yeates
  • P Quayle
چکیده

The regioselective, orthogonal functionalisation of 4,10-dichlorochrysene enables the synthesis of a variety of 2,8,4,10-"A2B2"-tetrasubstituted chrysenes. Such compounds exhibit broadened UV-vis absorption spectra, decreased band gap and higher HOMO levels compared to the parent chrysene.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Iron-Catalyzed Oxidative C-H Functionalization of Internal Olefins for the Synthesis of Tetrasubstituted Furans.

Tetrasubstituted furans were efficiently synthesized from Fe(OAc)2-catalyzed C-H/C-H cross-dehydrogenative-coupling (CDC) reactions of activated carbonyl methylenes with S,S-functionalized internal olefins, that is, α-oxo ketene dithioacetals and analogues, under oxidative conditions. β-Ketoesters, 1,3-dicarbonyls, β-keto nitrile, and amide derivatives were used as the coupling partners. The re...

متن کامل

Strongly Phosphorescent Iridium(III)–Porphyrins – New Oxygen Indicators with Tuneable Photophysical Properties and Functionalities

Synthesis and characterization of four iridium(III)-octaethylporphyrins and a π-extended iridium(III)-benzoporphyrin are presented. Strong room-temperature phosphorescence was observed for all of the complexes with quantum yields of up to 30 %. Axial ligands were introduced to tune the photophysical properties and the solubility. Complexes bearing lipophilic ligands such as pyridine or N-(n-but...

متن کامل

Synthesis of tetra-substituted phenanthroimidazole derivatives using SBA-Pr-SO3H

A one pot four-component reaction of 9,10-phenanthraquinone, aromatic aldehyde, aniline, and ammonium acetate was designed for the preparation of tetrasubstituted imidazoles (phenanthro[9,10-d]imidazole) derivatives in the presence of SBA-Pr-SO3H as a mesoporous solid acid catalyst. Phenanthro[9,10-d]imidazole derivatives were produced by the use of this technique in short reaction times and go...

متن کامل

NaHSO4-SiO2: An Efficient Reusable Green Catalyst for Selective C-3 Propargylation of Indoles with Tertiary Propargylic Alcohols

Although several methods for the preparation of 4o propargyl indole derivatives have been published, this synthetic transformation is complicated by the tendency of 3o propargyl alcohols to form allenium intermediates in acidic media.  It is therefore a challenge to find an efficient method for the C-3 propargylation of indoles with 3° propargylic alcohols.  In this pa...

متن کامل

Occurrence and Distribution of Chrysene and its Derivatives in Crude Oils and Source Rock Extracts from Niger Delta, Nigeria

Crude oils and source rocks from the northern and offshore Niger Delta basin, Nigeria, have been characterized by gas chromatography-mass spectrometry in terms of their origin and thermal maturity based on the distribution of chrysene and its derivatives. The crude oils and source rocks were characterized by the dominance of chrysene over benzo[a]anthracene. 3-methylchrysene predominated over o...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical communications

دوره 51 28  شماره 

صفحات  -

تاریخ انتشار 2015