Abstract
We describe the synthesis and photophysical properties of tetraarylnaphthidines. Our synthetic approach is based on an iron-catalyzed oxidative C–C coupling reaction as the key step using a hexadecafluorinated iron–phthalocyanine complex as a catalyst and air as the sole oxidant. The N,N,N’,N’-tetraarylnaphthidines proved to be highly fluorescent with quantum yields of up to 68%.
Highlights
2.12..S1Fy. onSltylhonewtshiisensgis a procedure reported by Nechaev et al for the Buchwald–Hartwig reaction under ssboorloluvvmneeFdnnootetnF-l-rlfaforrpeslewlhoeeoitlnwvhccgeaioonnlneangtnd-dpfeiiratrtei(ioo2oepc)nnercstsdooocuna[e[r11dfdef99iout]]ri,r,reodepnwwo1sre-ree(t[pde1hodhi9praa]thb,vveyeeedwnNyeaableccayhchmhaiiNeeavivnveeeeoevcdd)ahnecaathettphhaivehlee.vtehfetcocdaoorlaueuttlnp.hpheleeliin(nfB3cgog)ouriucnoohptfhfwhlieinadgdglhiBidppu–yohhHcifeeehnnaldwdyryitlalp(waaSlhmdmcieg–hiinnHnerymeeealaarec(tm(t1w11i))i)oin.gneaannur(dedn1ad)ce11tari--nodn bro1m-boronmapohntahpahlethnael(e2n)eto(2a)ftfooradffo1r-(dd1ip-(hdeinpyhleanmyilnamo)innaop)hntahpahltehnaele(3n)ei(n3)hinghhiygiheldyi(eSldch(eSmchee1m).e 1)
The fluorescence spectra were measured on a Varian Cary Eclipse spectrophotometer
The fluorescence lifetime was measured with an Edinburgh Instruments mini-τ by excitation with pulses of an EPLED (Edinburgh picosecond Pulsed Light Emitting Diode) (360 nm, 20 kHz) and time-resolved photon counting (TCSPC)
Summary
MolecuOlesn2020i,r2r5a,dxiFaOtiRonPEERwRiEtVhIEWUV-light (λex = 254 nm) in methanolic solution,[7] of 113(diphenylamino)naphthalene (3) and the resulting N,N,N’,N’-tetraarylnaphthidines 4 and 5 show a. 111,6540,0700000 a UV nanabpashpotrhhptithdioiindnein5mea4ximum; b m29o12la9r1 extinction co61e01f0f,i04c0ie0nt; c fluores4c4e45n63ce emission15m156a2ximum aλ(eeUxxc=Vit2aa9tb1nisonoanmrppa)ht;titodλhnSeixtdmo=kian2exs9eim1s5hnuifmmt, ;)∆;bλd =mStλooelkamre−sesx2λhta9ibin1sfc.t,tiΔonλ c=oλeffiemc–ienλta;b6s.c00fl0uorescence emis4s5io3n maximum (1e6xc2itation at a UV absorption maximum; b molar extinction coefficient; c fluorescence emission maximum (excitation at λex = 291 nm); d Stokes shift, Δλ = λem – λabs. NNoorrmmaalliizzeedd fflluuoorreesscceennccee eemmiissssiioonn ssppeeccttrraa of 1-(diphenylaammiinnoo))nnaapphhtthhaalleennee ((33)) (blue),, NN,NN,NN’,NN’-tetraphenylnaphthidiinnee (4) (orange), and naphthidine 5 (green) in methanol (excitation at Fλλiegxx u==r2e299181.nnmNmo)).r.malized fluorescence emission spectra of 1-(diphenylamino)naphthalene (3) (blue), N,N,N’,N’-tetraphenylnaphthidine (4) (orange), and naphthidine 5 (green) in methanol (excitation at λex = 291 nm). Methanol λabs (nm) a λem (nm) b a UV absorption maximum and b fluorescence emission maximum (for each solvent λex = λabs)
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