Eumelanin-inspired core derived from vanillin: a new building block for organic semiconductors.

نویسندگان

  • Subhashini Selvaraju
  • K A Niradha Sachinthani
  • RaiAnna A Hopson
  • Frederick M McFarland
  • Song Guo
  • Arnold L Rheingold
  • Toby L Nelson
چکیده

An eumelanin-inspired core derived from the natural product, vanillin (vanilla bean extract) was utilized for the synthesis of eumelanin-inspired small molecules and polymer via Sonogashira cross coupling. The materials demonstrate that the methyl 4,7-dibromo-5,6-dimethoxy-N-methyl-1H-indole-2-carboxylate core can serve as a new building block for organic semiconductors.

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

The Melanins – A Class of Bio-organic Conductor

The melanins are an important class of pigmentary macromolecule found throughout nature. Eumelanin is the predominant form in humans, and acts as our primary photoprotectant. The structure-property-function relationships that dictate the behavior of these biomaterials are still poorly understood. In particular, major questions still remain concerning the basic structural unit. It is well accept...

متن کامل

Mechanochemical synthesis of graphene oxide-supported transition metal catalysts for the oxidation of isoeugenol to vanillin

Vanillin is one of the most commonly used natural products, which can also be produced from lignin-derived feedstocks. The chemical synthesis of vanillin is well-established in large-scale production from petrochemical-based starting materials. To overcome this problem, lignin-derived monomers (such as eugenol, isoeugenol, ferulic acid etc.) have been effectively used in the past few years. How...

متن کامل

UV-dissipation mechanisms in the eumelanin building block DHICA.

The UV-dissipative mechanisms of the eumelanin building block 5,6-dihydroxyindole-2-carboxylic acid (DHICA) and the 4,7-dideutero derivative (DHICA-d(2)) in buffered H(2)O or D(2)O have been characterized by using ultrafast time-resolved fluorescence spectroscopy. Excitation of the carboxylate anion form, the dominating state at neutral pH, leads to dual fluorescence. The band peaking at lambda...

متن کامل

The exceptionally rich coordination chemistry generated by Schiff-base ligands derived from o-vanillin.

Ortho-vanillin became very popular in coordination chemistry because of its Schiff bases, which generate a rich variety of complexes, ranging from oligonuclear species to coordination polymers. Some of these organic molecules are particularly useful in metallosupramolecular chemistry for assembling homo- and heterometallic helicates. The Schiff bases obtained using aminoalcohols open the door t...

متن کامل

Synthesis of Benzothiadiazole Derivatives by Applying C-C Cross-Couplings.

The benzothiadiazole moiety has been extensively exploited as a building block in the syntheses of efficient organic semiconducting materials during the past decade. In this paper, parallel synthetic routes to benzothiadiazole derivatives, inspired by previous computational findings, are reported. The results presented here show that various C-C cross-couplings of benzothiadiazole, thiophene, a...

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 14  شماره 

صفحات  -

تاریخ انتشار 2015