1,6-Dihydroxynaphthalene CAS 575-44-0

Qhov sib xyaw no ua lub luag haujlwm tseem ceeb ua cov organic synthesis nruab nrab hauv cov txheej txheem tshuaj synthesis. Ob pawg hydroxyl ua haujlwm thiab ib lub nplhaib naphthalene hauv nws cov qauv muab ntau qhov chaw ua haujlwm rau tshuaj lom neeg, ua rau cov khoom sib xyaw ua ke los koom nrog ntau hom tshuaj lom neeg xws li acid-base neutralization, hloov pauv, thiab hloov pauv. Los ntawm kev qhia cov khoom sib txawv lossis cov hloov pauv, 2,5-dihydroxynaphthalene derivatives nrog cov haujlwm tshwj xeeb tuaj yeem npaj tau. Cov derivatives no muaj kev siv dav dav hauv cov teb xws li tshuaj, tshuaj tua kab, tshuaj zawv plaub hau, thiab lwm yam. Nws tuaj yeem ua cov khoom siv raw rau kev tsim cov organic molecules complex.

Daim ntawv thov ntawm no compound nyob rau hauv lub chaw kws tshuaj yog feem ntau yog reflected nyob rau hauv tshuaj synthesis. Los ntawm kev hloov kho tshuaj thiab kev hloov pauv, cov tebchaw nrog cov tshuaj pharmacological tuaj yeem npaj tau, uas ua lub luag haujlwm tseem ceeb hauv kev tsim tshuaj thiab kev kho mob. Kev tshawb fawb tau pom tias qee yam derivatives muaj kev tiv thaiv- qog nqaij hlav thiab tuaj yeem cuam tshuam kev loj hlob thiab kis ntawm cov qog hlwb. Cov tebchaw no muab cov tswv yim tshiab rau kev txhim kho cov tshuaj tiv thaiv- qog nqaij hlav. Qee cov derivatives kuj muaj cov tshuaj tiv thaiv - mob, uas tuaj yeem txo cov kev mob tshwm sim thiab mob.

Cov tshuaj no muaj peev xwm siv tau rau hauv kev tsim cov tshuaj tiv thaiv - mob. Nyob rau hauv tus txheej txheem ntawm kev tsim tshuaj, thawj kauj ruam yog los tshuaj xyuas thiab tshuaj xyuas cov compound thiab nws cov derivatives los txiav txim seb lawv puas muaj cov tshuaj pharmacological. Raws li kev soj ntsuam cov txiaj ntsig, ua kom zoo dua cov qauv ntawm cov tshuaj nquag los txhim kho lawv cov txiaj ntsig thiab txo cov kev mob tshwm sim. Tom qab kev txhim kho cov txheej txheem, qhov sib xyaw yuav tsum tau mus rau kev sim tshuaj ntsuam xyuas nws txoj kev nyab xeeb thiab kev ua tau zoo.

Cov khoom sib xyaw no muaj txiaj ntsig tseem ceeb hauv kev lag luam dyeing. A series ntawm acidic media dyes tuaj yeem npaj los ntawm kev sib txuas nrog ntau yam diazo. Cov dyes no tsuas yog siv rau dyeing thiab luam ntawv textiles xws li txhob lo lo ntxhuav, cashmere, thiab ntaub plaub. Cov dyes synthesized los ntawm nws muaj ci thiab ntev - cov xim kav ntev, uas tuaj yeem ua tau raws li cov xim siab ntawm textiles. Cov dyes muaj kev ntxuav zoo thiab lub hnub tiv thaiv, thiab tuaj yeem tswj cov xim ruaj khov thiab ci ntsa iab thaum siv sijhawm ntev -. Nyob rau hauv tus txheej txheem ntawm txhob lo lo ntxhuav dyeing, kev siv cov kua qaub mordant dyes synthesized los ntawm nws muaj peev xwm ua tiav cov xim ci thiab mos tes hnov ​​dyeing teebmeem. Nyob rau hauv cov txheej txheem luam ntawv, cov dyes kuj tuaj yeem muab cov qauv meej meej thiab muag muag, ua tau raws li qhov xav tau ntawm textile printing.

Cov compound no thiab nws cov derivatives kuj muaj qee qhov kev siv tau zoo hauv cov khoom siv luminescent. Los ntawm kev qhia cov khoom sib txawv lossis cov hloov pauv rau hauv cov molecule, nws cov khoom luminescent tuaj yeem hloov kho, ua tiav kev tswj hwm ntawm cov xim luminescent thiab fluorescence siv. OLED yog ib hom tshiab ntawm cov cuab yeej siv tshuab uas muaj qhov zoo xws li kev tso tawm tus kheej, cov xim ci, thiab qhov pom dav. Nws thiab nws cov derivatives tuaj yeem ua cov khoom siv luminescent rau OLEDs, muab qhov muaj peev xwm tshiab rau kev tsim cov thev naus laus zis.

Fluorescent probes yog cov tebchaw uas siv rau kev sau tshuaj lom neeg thiab cov duab kos duab . 2,5-dihydroxynaphthalene thiab nws cov derivatives tuaj yeem siv los ua cov ntaub ntawv raw rau fluorescent probes, thiab sojntsuam molecules nrog cov khoom siv fluorescent tshwj xeeb tuaj yeem npaj los ntawm kev hloov kho tshuaj lom neeg thiab kev hloov pauv rau kev tshawb nrhiav thiab kev ntsuam xyuas ntawm biomolecules. Lub tshuab hluav taws xob yog ib qho cuab yeej siv los ntsuas qhov concentration ntawm cov tshuaj lom neeg.

Kev ntsuas kev ua haujlwm ceev tau ua tiav ntawm cov pa roj-theem 1,6-DHN molecules siv B3LYP/6-311G (d, p) lub hauv paus ua haujlwm: 10 sp ² hybridized carbon atoms nyob rau hauv naphthalene nplhaib tsim ib lub ntiaj teb no skeletons hydrogen π - conjele atoms ntawm txoj haujlwm 1 thiab 6 thauj electrons mus rau lub nplhaib naphthalene los ntawm p - π conjugation, nce qib HOMO zog thiab txo qis LUMO zog.

Lub intrinsic HOMO yog -5.32 eV, LUMO yog -2.47 eV, thiab lub zog theem sib txawv Δ E yog 2.85 eV, sib xws rau intrinsic absorption wavelength ntawm 435 nm. Piv nrog cov tsis hydroxyl naphthalene (Δ E=3.32 eV, nqus ntawm 374 nm), cov hluav taws xob pub dawb ntawm cov pab pawg dihydroxy ua rau liab hloov ntawm 61 nm hauv kev nqus, uas yog qhov tseem ceeb rau cov molecule fluorescence nyob rau thaj tsam pom lub teeb.

Qhov kev npaj ntawm spatial ntawm hydroxyl pawg ua rau lub sijhawm molecular dipole ntawm μ=3.87 D, uas yog siab dua li ntawm symmetric 1,4-DHN (μ=1.12 D). Cov nyhuv dipole muaj zog ua rau cov molecule rau kev daws cov xim nyob rau hauv polar solvents (Solvatochromism): nyob rau hauv tsis yog -polar n-hexane, molecular hydrogen bonds nruj, HOMO-LUMO band sib txawv nce, thiab qhov siab tshaj plaws emission yog λ ₑₘ nblue ({8}); Cov pab pawg hydroxyl nyob rau hauv ncov qaumteb qabteb DMSO tsim intermolecular hydrogen bonds nrog cov kuab tshuaj, ua rau ntxiv delocalization ntawm electron huab thiab nqaim ntawm band sib txawv. Lub wavelength ntawm λ ₑₘ yog 517 nm (lub teeb ntsuab), thiab Stokes hloov ntawm 89 nm mus rau 152 nm. Qhov loj Stokes hloov tau zoo kom tsis txhob muaj kev cuam tshuam ntawm lub teeb ci ntsa iab thiab tsim nyog rau kev txhim kho fluorescent probes.

Hauv cov tshuaj dilute (concentration Tsawg dua los yog sib npaug rau 1 × 10 ⁻⁵ mol / L), 1,6-DHN tshwm sim raws li ib qho molecule cais tsis muaj intermolecular π - π stacking. Tom qab excitation los ntawm lub teeb ultraviolet (320-350 nm), hauv av xeev S ₀ electrons hloov mus rau S ₁ zoo siab singlet xeev, thiab 91% ntawm lub xeev zoo siab electrons rov qab los rau hauv av los ntawm kev hloov pauv hluav taws xob, tso tawm photons. Qhov seem 9% dissipates lub zog los ntawm kev vibrational so tsis muaj hluav taws xob dissipation. Lub fluorescence quantum tawm los ntawm cov tshuaj dilute yog Φ _f=0.38.

Txoj kev hloov pauv: S ₀ → S ₁ (π → π *) yog qhov hloov pauv loj, nrog n → π * kev hloov pauv nyiaj tsawg dua 5%. Tsis muaj TICT (intramolecular charge transfer quenching) ob txoj hauv kev, yog li cov fluorescence efficiency ntawm dilute tov yog ruaj khov thiab tsis cuam tshuam los ntawm kab polar impurities.

Thaum pH ntawm cov tshuaj hloov pauv, hydroxyl deprotonates los tsim cov phenoxide anions, thiab O ⁻ muaj lub zog hluav taws xob pub dawb muaj peev xwm, txuas ntxiv nthuav dav π electron delocalization. Lub HOMO nce los ntawm 0.42 eV, thiab Δ E poob rau 2.37 eV, emitting lub teeb liab hloov mus rau 602 nm, ua tiav pH ua rau xiav ntsuab ntsuab hloov pauv hloov. Qhov no protonation deprotonation reversible spectral hloov pauv yog lub hauv paus theoretical rau kev tsim qauv piv ntawm pH probes.

Lub xeev aggregation luminescence ntawm 1,6-DHN yog lub hauv paus txoj kev xav ntawm nws cov khoom siv- xeev luminescent. Raws li cov concentration / kua dej cov ntsiab lus nce, cov molecule hloov zuj zus los ntawm ib leeg-molecule mus xoob aggregation thiab tom qab ntawd mus rau ntom stacking, nthuav tawm bidirectional tunability ntawm aggregation quenching (ACQ) thiab aggregation induced luminescence (AIE), txawv ntawm cov tshuaj tsw qab ib txwm muaj ACQ:

Oligomerization (dej cov ntsiab lus 30% ~ 50%, molecular spacing 0.6 ~ 0.8 nm): Intermolecular hydroxyl hydrogen bonds dominate, π - π kev sib cuam tshuam tsis muaj zog, intramolecular hydroxyl twisting yog txwv los ntawm hydrogen daim ntawv cog lus, tsis muaj hluav taws xob hloov pauv tau cuam tshuam, qhov kev faib ua feem ntawm lub xeev radiative nce ntxiv yield nce los ntawm 0.38 mus rau 0.52, nthuav tawm cov yam ntxwv AIE (kev sib sau luminescence li);

High aggregation (water content>70%, qhov sib txawv molecular<0.4 nm): Large area π - π stacking of naphthalene rings forms H-aggregates, S ₁ excited state energy level splits, excited state energy is non radiative dissipated through exciton coupling, fluorescence quantum yield drops sharply to 0.07, and classical ACQ aggregation quenching occurs.
Txoj hauv kev tseem ceeb rau kev hloov kho OLED cov khoom- lub xeev lub teeb- emitting txheej yog kom kaw hauv oligomeric aggregates thiab mus tas li ua tiav AIE hom khoom - xeev luminescence los ntawm sab saw alkyl hloov kho thiab cyclodextrin suav nrog.

Nws kuj tseem siv tau rau kev sib txuas ntawm cov tshuaj tua kab. Los ntawm kev hloov kho tshuaj thiab kev hloov pauv, cov khoom siv tshuaj tua kab nrog tshuaj tua kab, kab mob bactericidal, lossis tshuaj tua kab mob tuaj yeem npaj tau. Cov khoom siv tshuaj tua kab no muab kev lees paub tseem ceeb rau kev ua liaj ua teb. Nws tseem tuaj yeem ua cov khoom siv raw lossis nruab nrab rau cov tshuaj zoo. Los ntawm kev cuam tshuam nrog lwm cov tebchaw, cov tshuaj zoo nrog cov haujlwm tshwj xeeb thiab siv tau tuaj yeem npaj tau, xws li surfactants, plasticizers, nplaim retardants, thiab lwm yam. Cov tshuaj zoo no muaj ntau yam ntawm cov nqi siv hauv kev tsim khoom. Nrog rau kev txhim kho txuas ntxiv ntawm kev tshawb fawb thiab thev naus laus zis, nws daim ntawv thov kev lag luam tseem niaj hnub nthuav dav. Nyob rau hauv lub neej yav tom ntej, qhov sib xyaw no tuaj yeem ua kom pom cov ntawv thov tshiab hauv thaj chaw xws li lub zog tshiab, cov ntaub ntawv zoo ib puag ncig, thiab biomedicine.