Synthesis and crystallographic study of 1,6 -bis -(N -phenothiazinyl ) -2,4 -hexadiyne

Chantana SAE-LIM; Daniel J SANDMAN; Bruce M FOXMAN; Mongkol SUKWATTANASINITT

doi:10.1080/10601320600996114

Back

Conference proceeding

Synthesis and crystallographic study of 1,6 -bis -(N -phenothiazinyl ) -2,4 -hexadiyne

Chantana SAE-LIM, Daniel J SANDMAN, Bruce M FOXMAN and Mongkol SUKWATTANASINITT

Journal of macromolecular science. Pure and applied chemistry, Vol.43(12), pp.1929-1936

Selected papers from the University of Massachusetts-Lowell 6th technical symposium in honor of professor Sukant K. Tripathy

2006

DOI: https://doi.org/10.1080/10601320600996114

Abstract

Chemistry

Heterocyclic compounds

Preparations and properties

Exact sciences and technology

Polydiacetylene

Organic Chemistry

1,6‐bis‐(N‐phenothiazinyl)‐2,4‐hexadiyne (I) was synthesized in high yield by oxidative coupling of N‐propargyl phenothiazine. Grown from methylene chloride‐hexane solution, I is a monoclinic crystal, space group C2/c a=14.9500(18) Å; b=13.5512(15) Å; c=12.0116(10) Å; β=102.628(9)° Å; V=2374.6(4) Å3. The intermolecular distances and arrangement of I in the unit cell preclude the usual diacetylene reactivity. Nevertheless, heating of I at 145°C results in decomposition of I to phenothiazine and a dark brown solid. In addition, cation‐radicals of I were prepared by oxidation with nitrosonium tetrafluoroborate and iodine to give stable ion‐radical salts.

Metrics

15 Record Views

Details

Title: Synthesis and crystallographic study of 1,6 -bis -(N -phenothiazinyl ) -2,4 -hexadiyne
Creators: Chantana SAE-LIM - Center for Advanced Materials, Department of Chemistry, University of Massachusetts Lowell, Lowell, MA, United States
Daniel J SANDMAN - Center for Advanced Materials, Department of Chemistry, University of Massachusetts Lowell, Lowell, MA, United States
Bruce M FOXMAN - Department of Chemistry, Brandeis University, Waltham, MA, United States
Mongkol SUKWATTANASINITT - Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand
Publication Details: Journal of macromolecular science. Pure and applied chemistry, Vol.43(12), pp.1929-1936
Conference: Selected papers from the University of Massachusetts-Lowell 6th technical symposium in honor of professor Sukant K. Tripathy
Publisher: Taylor & Francis
Identifiers: 9923989593301921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Conference proceeding

Synthesis and crystallographic study of 1,6 -bis -(N -phenothiazinyl ) -2,4 -hexadiyne

Abstract

Metrics

Details

Brandeis University Social media