Synthesis and properties of 6-(hydroxymethyl)-9,9,10,10-tetracyanonaphthoquinodimethane

Torres, E.; Panetta, Charles A.; Heimer, Norman E.; Clark, B.J.; Hussey, Charles L.

doi:10.1021/jo00011a061

Cited by 21 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The assembly technique chosen by the Organic Rectifier Project at the University of Mississippi (1982−1991) by Charles A. Panetta, Metzger, and collaborators was the LB method. Many molecules were made which did indeed form LB films (structures 35 − 43 in Figure , and Tables and ). − ,− ,,,,,, They were all obtained by using the carbamate coupling reaction as the last synthetic step (it was not possible to convert a weak acceptor into a strong acceptor in the presence of a strong donor after the covalent bridge is already built; rather, the coupling reaction must strongly favor the bridge building over the competing formation of an ionic charge-transfer salt). An ester coupling was also successful.…”

Section: The Organic Rectifier Projectmentioning

confidence: 99%

See 1 more Smart Citation

Unimolecular Electrical Rectifiers

2003

View full text Add to dashboard Cite

research with H. M. McConnell) and post-docs at Stanford (research with P. G. Simpson and M. Boudart), Metzger taught Italian at Stanford (1970− 1971) and chemistry at the University of Mississippi (1971−1986) and the University of Alabama (1986 to present), where he is Professor of Chemistry and former Tricampus Director of the Materials Science Ph.D. Program. Metzger has published 188 papers, edited three books, obtained one patent, graduated 12 Ph.D.'s and 1 M.S., directed the research of 15 undergraduates, and gave talks or spent sabbatical or other leaves in 22 countries. In 1984, he became the first Coulter Professor of Chemistry at the University of Mississippi. In 1998, he received the Blackmon-Moody award of the University of Alabama for exceptional research.

show abstract

Section: The Organic Rectifier Projectmentioning

confidence: 99%

“…A final acceptor was HMTCNaQ, 49 . Its crystal structure has been determined; however, it decomposed instead of coupling with phenyl, 4-(dimethylamino)phenyl, or 1-pyrenyl isocyanates 9 Monofunctionalized donors ( 44 − 46 ) and monofunctionalized acceptors ( 47 − 49 ). …”

Section: The Organic Rectifier Projectmentioning

confidence: 99%

Unimolecular Electrical Rectifiers

2003

View full text Add to dashboard Cite

show abstract

“…Special interest has been devoted during the last few years by Bryce, Martı ´n, Panetta and others to the synthesis of new TCAQ derivatives 12, 22 13, 23 14, 24 15, 25 16 26 and 17 26 (Fig. 6) endowed with functional groups that have allowed their further incorporation into more complex molecular and macromolecular architectures, giving rise to a variety of interesting electroactive materials whose properties will be discussed later on this article.…”

Section: Synthesis Of Tcaq and Derivativesmentioning

confidence: 99%

The first two decades of a versatile electron acceptor building block: 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ)

2007

View full text Add to dashboard Cite

This critical review surveys the development of the structural and electrochemical knowledge of the TCAQ moiety since its discovery, nearly two decades ago, until the present. Additionally, recent advances in the chemistry and functionalization of this versatile building block are highlighted, with special emphasis on the strategies devoted to the preparation of donor-acceptor molecular and polymeric materials. The applications of TCAQ-based materials in materials science as electrical conductors, molecular rectifiers, in photoinduced electron transfer processes, optoelectronic devices and as electrochiroptical materials are also reviewed (89 references).

show abstract

“…As known, the most frequently used method for the conversion of 1,4-benzoquinone to 1,4-naphthoquinone derivatives utilizes the conventional Diels-Alder reaction pathway by involving 1,3-butadiene derivative as the dienophile. [38][39][40][41][42][43] Yet, there were no 1,3-butadiene derivatives to start with in the aforementioned reactions executed. Therefore, the reaction pathways for the formation of 3-like compounds must be unprecedented routes.…”

Section: Proposed Mechanism For the Formations Of 3b And 3dmentioning

confidence: 99%

Tertiary amines as vinyl source for the formations of aryl or pyrrole ring on amido‐substitued 1,4‐quinone with the assistance of palladium salt

Jhou

Cheng

Hong

2020

J Chinese Chemical Soc

View full text Add to dashboard Cite

The one-pot synthesis of 3-isopropyl-6-methyl-1H-benzo[f]indole-4,9-dione (3e), N-(4-[isopentylamino]-3,6-dioxocyclohexa-1,4-dien-1-yl)acetamide (4d), 2-(isopentylamino)-6-methylnaphthalene-1,4-dione (5b), and 2-(4-acetamido-3,6-dioxocyclohexa-1,4-dien-1-yl)-N,N-diisopentyl-3-methylbutanamide (6a) has been achieved via either pyrrol/aryl ring formations or amination reactions from the Pd(II)-catalyzed reaction of N-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetamide (2a_BQ) and in the presence of triisopentylamine. More 3-, 4-, 5-, and 6-like derivatives were obtained while other trialkylamines were used. Crystal structures of 3d_O, 3e, 4b, 4c, 4d, 5b, and 6a were determined by single-crystal X-ray diffraction methods. The 3-and 5-like products reveal the formations of newly generated benzene rings with/without substitutions. The formation of 6a also implies an unusual reaction pathway of its generation. Based on the structural conformations of various 3-like products, as well as 6a, mechanisms were proposed to account for the formations of these compounds. Various fascinating conformations of products observed in this work demonstrate the diversities of this type of reactions.

show abstract

Synthesis and properties of 6-(hydroxymethyl)-9,9,10,10-tetracyanonaphthoquinodimethane

Cited by 21 publications

References 0 publications

Unimolecular Electrical Rectifiers

Unimolecular Electrical Rectifiers

The first two decades of a versatile electron acceptor building block: 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ)

Tertiary amines as vinyl source for the formations of aryl or pyrrole ring on amido‐substitued 1,4‐quinone with the assistance of palladium salt

Contact Info

Product

Resources

About