Controlling the Emissive Activity in Heterocyclic Systems Bearing CP Bonds

The photophysical properties of a series of heteroatom substituted indoles are explored to identify chemical means to control their emissive activity. In particular, we consider impacts of changes in the conjugated backbone, where the CN bonds of benzoxazoles are replaced by CP bonds (benzoxaphospholes). The effects of extending the π-conjugation, incorporating various secondary heteroatoms (X–CP), and enforcing planar rigidity are also examined. Our computational analysis explains the higher fluorescence efficiency observed with extended π-conjugation and highlights the importance of maintaining molecular planarity at both ground- and emissive-state geometries

Fluorescent Heteroacenes with Multiply-Bonded Phosphorus

An air-stable primary phosphine, 2,6-diphosphinonaphthalene-1,5-diol (<b>4</b>), has been synthesized and structurally characterized. A series of π-conjugated heteroacenes containing two phosphaalkene (PC) units, 2,7-R₂-naphtho­[1,2-<i>d</i>:5,6-<i>d</i>′]­bi­(soxaphosphole)­s [R₂-NBOP, R = ^<i>t</i>Bu (<b>5a</b>), Ad (<b>5b</b>), and Ph (<b>5c</b>)], have been synthesized from reactions of <b>4</b> and benzimidoyl chlorides. These novel fluorescent analogues of organic acenes were characterized by multinuclear NMR, UV–vis, and fluorescence spectroscopy, cyclic voltammetry, and single-crystal X-ray diffraction experiments

Fluorescent Heteroacenes with Multiply-Bonded Phosphorus

An air-stable primary phosphine, 2,6-diphosphinonaphthalene-1,5-diol (<b>4</b>), has been synthesized and structurally characterized. A series of π-conjugated heteroacenes containing two phosphaalkene (PC) units, 2,7-R₂-naphtho­[1,2-<i>d</i>:5,6-<i>d</i>′]­bi­(soxaphosphole)­s [R₂-NBOP, R = ^<i>t</i>Bu (<b>5a</b>), Ad (<b>5b</b>), and Ph (<b>5c</b>)], have been synthesized from reactions of <b>4</b> and benzimidoyl chlorides. These novel fluorescent analogues of organic acenes were characterized by multinuclear NMR, UV–vis, and fluorescence spectroscopy, cyclic voltammetry, and single-crystal X-ray diffraction experiments

Fluorescent Heteroacenes with Multiply-Bonded Phosphorus

An air-stable primary phosphine, 2,6-diphosphinonaphthalene-1,5-diol (<b>4</b>), has been synthesized and structurally characterized. A series of π-conjugated heteroacenes containing two phosphaalkene (PC) units, 2,7-R₂-naphtho­[1,2-<i>d</i>:5,6-<i>d</i>′]­bi­(soxaphosphole)­s [R₂-NBOP, R = ^<i>t</i>Bu (<b>5a</b>), Ad (<b>5b</b>), and Ph (<b>5c</b>)], have been synthesized from reactions of <b>4</b> and benzimidoyl chlorides. These novel fluorescent analogues of organic acenes were characterized by multinuclear NMR, UV–vis, and fluorescence spectroscopy, cyclic voltammetry, and single-crystal X-ray diffraction experiments

Fluorescent Heteroacenes with Multiply-Bonded Phosphorus

An air-stable primary phosphine, 2,6-diphosphinonaphthalene-1,5-diol (<b>4</b>), has been synthesized and structurally characterized. A series of π-conjugated heteroacenes containing two phosphaalkene (PC) units, 2,7-R₂-naphtho­[1,2-<i>d</i>:5,6-<i>d</i>′]­bi­(soxaphosphole)­s [R₂-NBOP, R = ^<i>t</i>Bu (<b>5a</b>), Ad (<b>5b</b>), and Ph (<b>5c</b>)], have been synthesized from reactions of <b>4</b> and benzimidoyl chlorides. These novel fluorescent analogues of organic acenes were characterized by multinuclear NMR, UV–vis, and fluorescence spectroscopy, cyclic voltammetry, and single-crystal X-ray diffraction experiments