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  • 2-Bromo-9,9-dimethylfluorene CAS 28320-31-2 9,9-Dimethyl-2-bromofluorenone CAS no 28320-31-2 9H-Fluorene,2-bromo-9,9-dimethyl-

    Cas No: 28320-31-2

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28320-31-2 Usage

Chemical Properties

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Uses

2-Bromo-9,9-dimethylfluorene can be used as a conducting polymer in the fabrication of a variety of devices which include photoelectronic devices, organic light emitting diodes (OLEDs) and organic solar cells (OSCs).

General Description

2-Bromo-9,9-dimethylfluorene is a fluorene derivative which shows π-electron conjugation. It has a high fluorescent and high electron delocalization. It can be used as a non-linear optical (NLO) material. It can be synthesized by using 2-bromofluorene and iodomethane as the major reactants. It can be majorly used in organic electronic based applications.

Check Digit Verification of cas no

The CAS Registry Mumber 28320-31-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,3,2 and 0 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 28320-31:
(7*2)+(6*8)+(5*3)+(4*2)+(3*0)+(2*3)+(1*1)=92
92 % 10 = 2
So 28320-31-2 is a valid CAS Registry Number.
InChI:InChI=1/C15H13Br/c1-15(2)13-6-4-3-5-11(13)12-8-7-10(16)9-14(12)15/h3-9H,1-2H3

28320-31-2 Well-known Company Product Price

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  • Alfa Aesar

  • (H64732)  2-Bromo-9,9-dimethylfluorene, 98%   

  • 28320-31-2

  • 5g

  • 735.0CNY

  • Detail
  • Alfa Aesar

  • (H64732)  2-Bromo-9,9-dimethylfluorene, 98%   

  • 28320-31-2

  • 25g

  • 2352.0CNY

  • Detail
  • Alfa Aesar

  • (H64732)  2-Bromo-9,9-dimethylfluorene, 98%   

  • 28320-31-2

  • 100g

  • 6713.0CNY

  • Detail
  • Aldrich

  • (751472)  2-Bromo-9,9-dimethylfluorene  97%

  • 28320-31-2

  • 751472-1G

  • 988.65CNY

  • Detail

28320-31-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Bromo-9,9-dimethylfluorene

1.2 Other means of identification

Product number -
Other names 9,9-dimethyl-2-bromofluorene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:28320-31-2 SDS

28320-31-2Synthetic route

2-bromo-9H-fluorene
1133-80-8

2-bromo-9H-fluorene

methyl iodide
74-88-4

methyl iodide

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
Stage #1: 2-bromo-9H-fluorene With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃;
99%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dimethyl sulfoxide at 0℃; for 0.5h;99%
With potassium hydroxide; potassium iodide In dimethyl sulfoxide at 20℃; for 48h;97%
9,9-dimethyl-9H-fluorene
4569-45-3

9,9-dimethyl-9H-fluorene

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With sodium bromate; hydrogen bromide; trimethylbenzylammonium bromide In dichloromethane; water at 10 - 20℃; under 760.051 Torr; for 1.5h;90%
With N-Bromosuccinimide In dichloromethane at 20℃; for 24h;78%
With bromine; iron(III) chloride In water at 20℃; for 13h; Heating / reflux;20%
With bromine
C15H17Br

C15H17Br

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene67%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

acetyl chloride
75-36-5

acetyl chloride

1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)ethanone
899444-03-2

1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)ethanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 16h;99.3%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

methyl iodide
74-88-4

methyl iodide

2,9,9-trimethyl-9H-fluorene
69535-83-7

2,9,9-trimethyl-9H-fluorene

Conditions
ConditionsYield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
99%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

(2R*,3aR*,8bR*)-2-methyl-1,2,3,3a,4,8b-hexahydropenta[b]- indole

(2R*,3aR*,8bR*)-2-methyl-1,2,3,3a,4,8b-hexahydropenta[b]- indole

(2R*,3aR*,8bR*)-2-methyl-4-(9,9-dimethyl-9H-fluorenene-2-yl)- 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole

(2R*,3aR*,8bR*)-2-methyl-4-(9,9-dimethyl-9H-fluorenene-2-yl)- 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; tert-butyl XPhos In toluene Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;98%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

(1R*,3aR*,8bR*)-1-methyl-1,2,3,3a,4,8b-hexahydropenta[b]- indole

(1R*,3aR*,8bR*)-1-methyl-1,2,3,3a,4,8b-hexahydropenta[b]- indole

(1R*,3aR*,8bR*)-1-methyl-4-(9,9-dimethyl-9H-fluorenene-2-yl)- 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole

(1R*,3aR*,8bR*)-1-methyl-4-(9,9-dimethyl-9H-fluorenene-2-yl)- 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; tert-butyl XPhos In toluene Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;98%
N-phenyl-9H-carbazol-3-boronic acid
854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C33H25N

C33H25N

Conditions
ConditionsYield
With potassium phosphate tribasic trihydrate; C44H43B10Br2P; palladium diacetate In ethanol; toluene at 120℃; for 36h; Kinetics; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;98%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

2-bromo-7-iodo-9,9-dimethyl-9H-fluorene
319906-45-1

2-bromo-7-iodo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With potassium iodate; sulfuric acid; iodine; acetic acid In water at 80℃; for 2.5h;96%
With sulfuric acid; iodine; acetic acid; periodic acid In water at 50℃; for 5h;85%
With periodic acid dihydrate; sulfuric acid; iodine; acetic acid at 65 - 90℃; for 6.5h; Inert atmosphere;76%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

aniline
62-53-3

aniline

N-phenyl-(9,9-dimethyl-9H-fluoren-2-yl)amine
355832-04-1

N-phenyl-(9,9-dimethyl-9H-fluoren-2-yl)amine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene for 20h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;95%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 110℃; for 3.58333h; Inert atmosphere;93%
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 90℃; for 3h;92%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

2-phenylaniline
90-41-5

2-phenylaniline

N‐{[1,1'‐biphenyl]‐2‐yl}‐9,9‐dimethylfluoren‐2‐amine

N‐{[1,1'‐biphenyl]‐2‐yl}‐9,9‐dimethylfluoren‐2‐amine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene for 20h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;95%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene for 20h; Reflux;95%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 12h;94%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

3,4-(methylenedioxy)-benzeneboronic acid
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

C22H18O2

C22H18O2

Conditions
ConditionsYield
With C24H31Br2N3O9Pd; potassium carbonate In ethanol; water at 80℃; for 1.5h; Suzuki Coupling;95%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2-(2

2-(2"-methoxyphenyl)-9,9'-dimethylfluorene

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane at 20℃; for 6h;94%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C39H27NO

C39H27NO

C54H39NO

C54H39NO

Conditions
ConditionsYield
With tributylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 25h; Inert atmosphere;93%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

C21H17Cl

C21H17Cl

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere;93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere;90%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran at 80℃; for 5h; Inert atmosphere;85%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C15H9(2)H4Br

C15H9(2)H4Br

Conditions
ConditionsYield
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h;93%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-(9,9-dimethylfluorene-2-yl)-2-(trimethylsilyl)acetylene
950181-08-5

1-(9,9-dimethylfluorene-2-yl)-2-(trimethylsilyl)acetylene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 48h; Inert atmosphere;92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine Sonogashira Cross-Coupling;
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

triphenyl-(9,9-dimethylfluoren-2-yl)silane
1208005-82-6

triphenyl-(9,9-dimethylfluoren-2-yl)silane

Conditions
ConditionsYield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #2: Triphenylsilyl chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
92%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

2-(4-chlorophenyl)-9,9-dimethyl-9H-fluorene
1221237-82-6

2-(4-chlorophenyl)-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 2h; Inert atmosphere; Sealed tube;91%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 5h; Heating;88%
With palladium diacetate; sodium hydrogencarbonate; tris-(o-tolyl)phosphine In 1,2-dimethoxyethane; water at 90℃; for 5h; Schlenk technique; Inert atmosphere;75%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

4-Aminobiphenyl
92-67-1

4-Aminobiphenyl

N‑(biphenyl‑4‑yl)‑9,9‑dimethyl‑9H‑fluorene‑2‑amine
897671-69-1

N‑(biphenyl‑4‑yl)‑9,9‑dimethyl‑9H‑fluorene‑2‑amine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate In toluene for 24h; Reflux;91%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene for 24h; Reflux;91%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃;91%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C39H27NS

C39H27NS

C54H39NS

C54H39NS

Conditions
ConditionsYield
With tributylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 23h; Inert atmosphere;91%
3-bromo-9H-carbazole
1592-95-6

3-bromo-9H-carbazole

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

3-bromo-9-(9',9'-dimethyl-9H-fluoren-2-yl)-9H-carbazole
1207672-45-4

3-bromo-9-(9',9'-dimethyl-9H-fluoren-2-yl)-9H-carbazole

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In para-xylene Reflux;91%
benzo[b]thiophene-2-boronic acid
98437-23-1

benzo[b]thiophene-2-boronic acid

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

2-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]thiophene

2-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]thiophene

Conditions
ConditionsYield
Stage #1: benzo[b]thiophene-2-boronic acid; 2-bromo-9,9-dimethyl-9H-fluorene With potassium carbonate In 1,2-dimethoxyethane; water for 0.333333h; Inert atmosphere;
Stage #2: With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In 1,2-dimethoxyethane; water at 80℃; for 15h; Inert atmosphere;
91%
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

3,5-bis(9,9-dimethyl-9H-fluoren-2-yl)-1-chlorotriazine

3,5-bis(9,9-dimethyl-9H-fluoren-2-yl)-1-chlorotriazine

Conditions
ConditionsYield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With iodine; magnesium In tetrahydrofuran at 55℃; for 1h; Glovebox;
Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at 55℃; Glovebox;
90%
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With iodine; magnesium In tetrahydrofuran for 1h; Reflux;
Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at 50℃; for 12h; Cooling with ice;
75%
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With magnesium In tetrahydrofuran for 2h; Reflux;
Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at -10 - 20℃;
48%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

9,9-dimethyl-9H-fluoren-2-ol
959246-70-9

9,9-dimethyl-9H-fluoren-2-ol

Conditions
ConditionsYield
With water; sodium hydroxide at 100℃; for 8h;90%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C22H17N

C22H17N

C37H29N

C37H29N

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene at 100℃; for 16h; Inert atmosphere;90%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

9H-carbazole
86-74-8

9H-carbazole

9-(9',9'-dimethyl-9H-fluoren-2-yl)-9H-carbazole
866100-16-5

9-(9',9'-dimethyl-9H-fluoren-2-yl)-9H-carbazole

Conditions
ConditionsYield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 200℃; for 30h; Ullmann reaction;89.15%
With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In 5,5-dimethyl-1,3-cyclohexadiene for 15h; Reflux; Inert atmosphere;84%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

2-iodo-9,9-dimethyl-9H-fluorene
144981-85-1

2-iodo-9,9-dimethyl-9H-fluorene

Conditions
ConditionsYield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 24.5h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;
89%
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 24h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;
89%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

bis(biphenyl-4-yl)amine
102113-98-4

bis(biphenyl-4-yl)amine

C39H31N

C39H31N

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 4h; Inert atmosphere; Reflux;88%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C18H10N4

C18H10N4

C48H34N4

C48H34N4

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere;88%
2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

N-phenyl-N-(11,11’-dimethylbenzo[a]fluoren-9-yl)amine

N-phenyl-N-(11,11’-dimethylbenzo[a]fluoren-9-yl)amine

C40H33N

C40H33N

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 100℃;88%

28320-31-2Relevant articles and documents

On-surface polymerization on a semiconducting oxide: Aryl halide coupling controlled by surface hydroxyl groups on rutile TiO2(011)

Kolmer, Marek,Zuzak, Rafal,Ahmad Zebari, Amir A.,Godlewski, Szymon,Prauzner-Bechcicki, Jakub S.,Piskorz, Witold,Zasada, Filip,Sojka, Zbigniew,Bléger, David,Hecht, Stefan,Szymonski, Marek

, p. 11276 - 11279 (2015)

Based on scanning tunneling microscopy experiments, we show that the covalent coupling of aryl halide monomers on the rutile TiO2(011)-(2 × 1) surface is controlled by the density of surface hydroxyl groups. The efficiency of the polymerization reaction depends on the level of surface hydroxylation, but the presence of hydroxyl groups is also essential for the reaction to occur.

Octa(aminophenyl)silsesquioxane as a nanoconstruction site

Tamaki,Tanaka,Asuncion,Choi,Laine

, p. 12416 - 12417 (2001)

-

Rational Design of Push–Pull Fluorene Dyes: Synthesis and Structure–Photophysics Relationship

Shaya, Janah,Fontaine-Vive, Fabien,Michel, Beno?t Y.,Burger, Alain

, p. 10627 - 10637 (2016)

Our work surveyed experimental and theoretical investigations to construct highly emissive D–π–A (D=donor, A=acceptor) fluorenes. The synthetic routes were optimised to be concise and gram-scalable. The molecular design was first rationalised by varying the electron-withdrawing group from an aldehyde, ketotriazole or succinyl to methylenemalonitrile or benzothiadiazole. The electron-donating group was next varied from aliphatic or aromatic amines to saturated cyclic amines ranging from aziridine to azepane. Spectroscopic studies correlated with TD-DFT calculations provided the optimised structures. The selected push–pull dyes exhibited visible absorptions, significant brightness, important solvatofluorochromism, mega-Stokes shifts (>250 nm) and dramatic shifts in emission to the near-infrared. The current library includes the comprehensive characterization of 16 prospective dyes for fluorescence applications. Among them, several fluorene derivatives bearing different conjugation anchors were tested for coupling and demonstrated to preserve the photophysical responses once further bound.

Synthesis, characterization and third-order non-linear optical properties of novel fluorene monomers and their cross-conjugated polymers

Ramos-Ortíz,Maldonado,Hernández,Zolotukhin,Fomine,Fr?hlich,Scherf,Galbrecht,Preis,Salmon,Cárdenas,Chávez

, p. 2351 - 2359 (2010)

We designed and synthesized two novel fluorene monomers of D-A-D (donor-acceptor-donor) type (M1 and M2), and their two corresponding polymers (PM1 and PM2) and a copolymer (CPM). These high molecular weight, film-forming polymers were obtained from metal-free, superacid-catalyzed reactions of the monomers with N-phenylisatin. The cubic NLO response (χ(3)) for these new compounds, in solid thin films, was measured through the use of third-harmonic generation (THG) Maker-Fringes technique at IR wavelengths given values of the order of 10-12 esu from which, the corresponding second hyperpolarizabilities (γ) were estimated to be of the order of 10-33 esu for monomers and 10-31 esu for polymers. Second hyperpolarizabilities have also been estimated theoretically at B3LYP/6-31G(d) level of theory in gas phase and related with the electronic structure of the synthesized molecules.

Spirooxazine photochromic compound and preparation method thereof

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Paragraph 0016, (2020/06/17)

The invention discloses a spirooxazine photochromic compound and a preparation method thereof, and belongs to the technical field of organic functional materials. The molecular structure is disclosedin the invention, whereinR1 and R2 are hydrogen, C1-C6 alkyl (CH2, m = 1, 2, 3, 4, 5, 6), and benzyl; R3and R4 are hydrogen, halogen, C1-C6 alkyl (CH2, m = 1, 2, 3, 4, 5, 6). Accordingto the invention, a photothermal stable fluorene phenol structure is introduced; different groups are used for substitution; the advantages of a novel photochromic material with spirooxazine are provided; the light response speed is high; meanwhile, color fading is rapid, moreover, the photo-thermal stability is good, an open-loop state and a closed-loop state can stably exist for a long time; guidance is provided for solving the problem that the ring-opening state ofspirooxazine photochromic compounds is unstable; the photochromic compound with various color changes from colorless to red, yellow, green, blue or purple is realized, the color variety of color change is richer, the market diversification requirements are finally met, the synthesis raw materials are cheap and easily available, and the synthesis process is easy to realize industrialization.

Fused cyclic compound and organoelectroluminescent device comprising the compound

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Paragraph 0060-0066, (2018/10/24)

The present invention refers to novel fused ring compound and including organic light emitting diode relates to search, the present invention according to fused ring compounds including organic electroluminescent device which has a low driving voltage 1 by disclosed. (by machine translation)

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