Synthesis · Naphthalene Diimide-Based Hydrogen-Bonded Organic Framework for High Electrical Conductivity and Ammonia Sensor Applications

6 structured synthesis routes

Completeness describes how fully the route could be reconstructed from the main article and supporting information.

Partial recipeSource: Both

Route 1: Other

p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S20

Linker precursorsdrop-cast pristine NDI(CPOH)2-SC device

Atmosphereammonia gas after evacuating ambient air

Temperatureroom temperature

Timevaried during sensor cycles

Substrate orientationSC device connected to SMU

Oxidant / reductantammonia reductant/dopant under 365 nm UV irradiation

Work-upde-doped by purging ammonia and applying high vacuum

Activation365 nm UV irradiation at 10 mW cm-2 during doping

Scalability contextSensor/device-scale reversible gas exposure; ammonia pressure/flow rate not reported in text.

Show 1 structured reagent record

Role	Reagent	Amount / concentration	Source
Reductant	ammonia gas	flowed gas; amount not specified	p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S20

Complete recipeSource: Both

Route 2: Other

p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S3b

Linker precursorsdrop-cast NDI(CPOH)2-SCs

Atmosphereambient

Temperatureroom temperature

Time12-24

Substrate orientationSCs on SiO2/device substrate

Oxidant / reductanthydrazine monohydrate vapour reductant

Work-updirect vapour exposure; no workup specified

Activationnone for normal-treated Device B

Scalability contextPost-synthetic vapour doping of device crystals; no bulk throughput reported.

Show 1 structured reagent record

Role	Reagent	Amount / concentration	Source
Reductant	Hydrazine Monohydrate	vapour exposure	p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S3b

Complete recipeSource: Both

Route 3: Other

p.5 · 2.3. Electronic Characterization of NDI(CPOH)2-Based HOF · Figure 2c,d; Figure S13

Linker precursorsdrop-cast NDI(CPOH)2-SCs

Atmosphere10^-5 Pa vacuum pretreatment, then ambient hydrazine vapour exposure

Temperatureroom temperature

Time48 h vacuum pretreatment; 12-24 h hydrazine vapour exposure

Substrate orientationSCs on SiO2/device substrate

Oxidant / reductanthydrazine monohydrate vapour reductant

Work-updirect vapour exposure after vacuum pretreatment

Activation10^-5 Pa for 2 days before hydrazine doping

Scalability contextDevice-scale vacuum pretreatment improves hydrazine doping rate and conductivity.

Show 1 structured reagent record

Role	Reagent	Amount / concentration	Source
Reductant	Hydrazine Monohydrate	vapour exposure	p.5 · 2.3. Electronic Characterization of NDI(CPOH)2-Based HOF · Figure 2c,d; Figure S13

Complete recipeSource: Both

Route 4: Other

p.8 · 4. Experimental Section, Synthesis of NDI(CPOH)2 · Figure S1a

Linker precursors1,4,5,8-naphthalene tetracarboxylic dianhydride; (1R,2R)-2-aminocyclopentanol hydrochloride

Solventsdimethylformamide (DMF); methanol workup

Additivesdiisopropylethylamine (DIPEA)

Atmospherepressure-tight microtube; atmosphere not otherwise specified

Temperature80 then 140

Time0.167 at 80 deg C then 1 at 140 deg C; 72 h at 4 deg C after methanol addition

Work-up50 mL methanol added; kept at 4 deg C for 3 days; filtered yellow precipitate

Scalability contextReported at 1.0 mmol dianhydride scale with 70% yield.

Show 5 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	1,4,5,8-naphthalene tetracarboxylic dianhydride	1.0 mmol	p.8 · 4. Experimental Section, Synthesis of NDI(CPOH)2 · Figure S1a
Linker	(1R, 2R)-2-Aminocyclopentanol hydrochloride	2.1 mmol	p.8 · 4. Experimental Section, Synthesis of NDI(CPOH)2 · Figure S1a
Base	diisopropylethylamine (DIPEA)	2.5 mmol	p.8 · 4. Experimental Section, Synthesis of NDI(CPOH)2 · Figure S1a
Solvent	dimethylformamide (DMF)	Not specified	p.8 · 4. Experimental Section, Synthesis of NDI(CPOH)2 · Figure S1a
Solvent	methanol	50 mL	p.8 · 4. Experimental Section, Synthesis of NDI(CPOH)2 · Figure S1a

Complete recipeSource: Both

Route 5: Drop Cast

p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S3b

Linker precursorsNDI(CPOH)2 compound

SolventsDMF

Atmosphereambient

Temperatureroom temperature

Time48

Substrate orientationcleaned SiO2 substrate

Work-upambient solvent evaporation led to needle-shaped single crystals on SiO2

Activationnone before Device A; optional 10^-5 Pa, 2 d vacuum treatment before Device C

Scalability contextThin single-crystal device growth on substrate from 9 mg mL-1 solution; no bulk scale-up reported.

Show 2 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	NDI(CPOH)2	9 mg mL-1	p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S3b
Solvent	DMF	Not specified	p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S3b

Partial recipeSource: Both

Route 6: Other

p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S3a

Linker precursorsNDI(CPOH)2 compound

Atmospherenitrogen

Temperature300

Substrate orientationbetween two glass slides with spacers

Scalability contextQualitative crystal-growth method; amount and duration are not reported in the exposed text.

Show 1 structured reagent record

Role	Reagent	Amount / concentration	Source
Linker	NDI(CPOH)2 compound	Not specified	p.8 · 4. Experimental Section, Crystal Growth and Doping Method · Figure S3a