102153-44-6

Usage

Uses

2-Bromo-3-iodonaphthalene can be used as an organic LED for novel electroluminescent hosts.

Synthesis Reference(s)

Synthetic Communications, 33, p. 2751, 2003 DOI: 10.1081/SCC-120021997

InChI:InChI=1/C10H6BrI/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6H

Upstream product

• 13214-70-5 2,3-dibromonaphthalene 
• 110-00-9 furan 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 80789-65-7 10-bromo-1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8-dimethanotriphenylene 
• 623924-91-4 2-bromo-3-iodo-bis(hexachlorocyclopentadiene)naphthalene 
• 690244-08-7 1,3-dibromo-2-nitro-naphthalene 
• 106750-88-3 6,7-dibromo-1,4-epoxy-1,4-dihydronaphthalene 
• 54245-33-9 3-bromonaphthalen-2-amine 

Downstream Products

• 258-47-9 Dibenzo[b,h]biphenylene 

Relevant academic research and scientific papers

The metalation of 1- and 2-(trifluoromethyl)naphthalenes: Noteworthy site selectivities

This article provides insight into the various factors by which electronegative substituents affect the kinetic acidity of arenes and, more specifically, naphthalenes. Both 1- and 2-(trifluoromethyl)naphthalenes were consecutively treated with an organometallic or lithium dialkylamide-type base and carbon dioxide. Due to single electron-transfer triggered side reactions, the yields of (trifluoromethyl)naphthoic acids were moderate to poor. 1-(Trifluoromethyl)naphthalene was exclusively attacked at the 2-position as expected. The 2-isomer reacted with tert-butyllithium in the presence of potassium tert-butoxide solely at the 1-position, but with sec-butyllithium in the presence of N,N,N′,N′-tetramethylethylene-diamine concomitantly at the 3- and 4-positions. Authentic samples of the key acids 1, 4, 5 and 6 were prepared based on independent, unambiguous methods.

Facile synthesis of 2,3-diiodonaphthalene and 2-bromo-3-iodonaphthalene

2,3-Diiodonaphthalene (5) and 2-bromo-3-iodonaphthalene (6) were readily synthesized in two steps by iodination of the corresponding bis(hexachlorocyclopentadiene) adducts 1 and 3 of naphthalene and 2-bromonaphthalene, in methanesulfonic acid, followed by retro Diels-Alder reaction combined with sublimation.

Chrysene-Based Blue Emitters

Chrysene and its bisbenzannulated homologue, naphtho[2,3-c]tetraphene, were synthesized through a PtCl2-catalyzed cyclization of alkynes, which also furnished corresponding biaryls subsequent to a Glaser coupling reaction of the starting alkynes. The optoelectronic properties of 5,5′-bichrysenyl and 6,6′-binaphtho[2,3-c]tetraphene were compared to their chrysene-based “monomers”. Oxidative cyclodehydrogenations of bichrysenyl and its higher homologue towards large nanographenes were also investigated.

LIGHT-EMITTING MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, ORGANIC ELECTROLUMINESCENT DEVICE USING SAME, AND MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE

Disclosed are a novel aromatic compound having excellent light emitting efficiency and thermal stability, a manufacturing method thereof, and an organic electroluminescent device comprising the novel aromatic compound. According to the present invention, provided are an aromatic compound forming a ring, and a novel aromatic derivative represented by chemical formula 1, which improves performance of a device. In the chemical formula 1, Z is equally or differently N (nitrogen), O (oxygen), or S (sulfur) in each case. Also, when Z is N (nitrogen), L1 is an integer of 1, and when Z is O (oxygen) or S (sulfur), L1 is an integer of 0.COPYRIGHT KIPO 2015

HETEROACENE DERIVATIVE, TETRAHALOTERPHENYL DERIVATIVE, AND THEIR PRODUCTION METHODS

There are provided a heteroacene derivative having an excellent oxidation resistance and capable of forming a semiconductor active phase by a coating process, and an oxidation-resistant organic semiconductor material using the same, as well as an organic thin film. [Means for Resolution] heteroacene derivative represented by the formula (1) is obtained by tetrametalation of a tetrahaloterphenyl derivative with a metalation agent and subsequent treatment of the resulting compound with reaction agents: wherein the substituents R1 to R4 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, an aryl group having 4 to 30 carbon atoms, an alkyl group having 3 to 20 carbon atoms, or a halogenated alkyl group having 1 to 20 carbon atoms; T1 and T2 are the same or different and each represents sulfur, selenium, tellurium, oxygen, phosphorus, boron, or aluminum; 1 and m each is an integer of 0 or 1; and rings A and B are the same or different and each has a structure represented by the following formulae (A-1) or (A-2).

TERPHENYLENE DERIVATIVES, TETRAHALOTERPHENYL DERIVATIVES AND PROCESSES FOR THE PRODUCTION OF BOTH

The invention provides terphenylene derivatives which have excellent oxidation resistance and permit the formation of semiconductor active phases by coating; and oxidation-resistant organic semiconductor materials and organic thin films, made by using the same. The invention relates to production of terphenylene derivatives represented by the general formula (1) by tetralithiating a tetrahaloterphenyl derivative with a lithiating agent and then treating the obtained compound with a copper compound: (1) wherein R1 to R14 are each independently hydrogen, fluoro, chloro, aryl having 4 to 30 carbon atoms, alkynyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkyl having 1 to 20 carbon atoms, halogenated alkyl having 1 to 20 carbon atoms, or diarylamino having 8 to 30 carbon atoms; and l, m, and n are each an integer of 0 or 1.