Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives.
Mio Matsumura,Mizuki Yamada,Atsuya Muranaka,Misae Kanai,Naoki Kakusawa,Daisuke Hashizume,Masanobu Uchiyama,Shuji Yasuike +7 more
TLDR
The benzophosphole-fused indoles, such as phosphine oxide, phospholium salt, and borane complex, exhibited strong photoluminescence in dichloromethane (Φ = 67–75%).Abstract:
The parent benzophospholo[3,2-b]indole was prepared by the reaction of dichlorophenylphosphine with a dilithium intermediate, which was prepared in two steps from 2-ethynyl-N,N-dimethylaniline. Using the obtained benzophosphole-fused indole as a common starting material, simple modifications were carried out at the phosphorus center of the phosphole, synthesizing various functionalized analogs. The X-ray structure analysis of trivalent phosphole and phosphine oxide showed that the fused tetracyclic moieties are planar. The benzophosphole-fused indoles, such as phosphine oxide, phospholium salt, and borane complex, exhibited strong photoluminescence in dichloromethane (Φ = 67–75%).read more
Citations
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Copper-Catalyzed Direct Oxidative C-H Functionalization of Unactivated Cycloalkanes into Cycloalkyl Benzo[ b]phosphole Oxides.
TL;DR: The first simple and efficient Cu-catalyzed radical addition/cyclization of various unactivated cycloalkanes with diaryl(arylethynyl)-phosphine oxides has been developed, providing a general, one-step approach to construct a new class of important benzo[ b]phosphole oxides via sequential C-H functionalization along with two new C-C bond formations.
Journal ArticleDOI
Highly Fluorescent Benzophosphole Oxide Block-Copolymer Micelles
Sarah M. Parke,Susumu Tanaka,Haoyang Yu,Emanuel Hupf,Michael J. Ferguson,Yuqiao Zhou,Kensuke Naka,Eric Rivard +7 more
TL;DR: In this paper, a norbornene-appended benzophosphole oxide monomer was found to readily undergo living ring-opening metathesis polymerization with the Grubbs third-generation catalyst to yield either a homopolymer or block copolymers.
Journal ArticleDOI
Phosphindole fused pyrrolo[3,2-b]pyrroles: a new single-molecule junction for charge transport.
TL;DR: A new family of phosphindole fused ladder-type heteroacenes with a pyrrolo[3,2-b]pyrrole core were synthesized and characterized, which show good luminescence efficiency, high thermostability and tunable conductance.
Journal ArticleDOI
Azobisisobutyronitrile-Initiated Oxidative C-H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives.
TL;DR: The first metal-free and facile radical addition/cyclization of simple alcohols with diaryl(arylethynyl)phosphine oxides has been described with AIBN as radical initiator, affording an efficient and one-pot procedure to access a new class of hydroxymethyl benzo[b]phosphole oxides of potential application in organic materials via sequential C(sp3)-H/C(sp2)-H functionalization.
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Alkyne Insertion into P–C(sp2) Bonds as a Route to Fused Phospholes: Transition-Metal-Like Reactivity at Phosphorus
TL;DR: In this paper, a direct alkyne insertion reaction into the P-C(aryl) bonds of tungsten-coordinated phenyl-aryl phosphenium ions was reported.
References
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